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Here is a chemical reaction formula: Reactants are m1_m2_m3:NC1=C(C=C(C=C1)Cl)C(C(F)(F)F)(C#CC1CC1)O, amount is: 0.0 ;m1_m2_m3:C(=O)(N1C=NC=C1)N1C=NC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=CC2=C(C(OC(N2)=O)(C(F)(F)F)C#CC2CC2)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluoro-3-butyn-2-ol (15.00 g, 0.0518 mol) and 41.98 g (0.259 mol) of 1,1'-carbonyldiimidazole in 250 mL of dry THF was stirred under argon at 55° C. for 24 hours. The solvent was removed on a rotary evaporator and the residue was partitioned between 500 mL of ethyl acetate and 400 mL of water. The layers were separated and the aqueous phase was extracted once more with ethyl acetate. The combined ethyl acetate extracts were washed with 2×200 mL of 2% aqueous HCl, saturated aqueous NaHCO3, and brine. Drying over MgSO4, filtration, and removal of the solvent in vacuo provided 16.42 g of the title compound as a solid. Recrystallization from ethyl acetate-hexane afforded 12.97 g of analytically pure (±) 6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one as a white crystals. mp: 178°-180° C. 1H-NMR (CDCl3): 0.85 (m, 2H), 0.94 (m, 2H), 1.40 (m, 1H), 6.81 (d, J=8.5 Hz, 1H), 7.37 (dd, J=2.5, 8.5 Hz, 1H), 7.49 (d, J=2.5 Hz, 1H), 8.87 (br s, 1H). |
Here is a chemical reaction formula: Reactants are m3:C(C)N(CC)CC, amount is: 0.0 ;m1_m4_m2_m5:ClC=1C=CC2=C(C(OC(N2)=O)(C(F)(F)F)C#CC2CC2)C1, amount is: 0.0 ;m1_m4_m2_m5:C12(C(CC(CC1)C2(C)C)C(=O)Cl)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m5:ClCCl, amount is: 0.0 ,Catalysts are m1_m4_m2_m5:CN(C1=CC=NC=C1)C, amount is: 0.0 .Products are 0:ClC=1C=CC2=C(C(OC(N2C(=O)C2[C@@]3(CCC(C2)C3(C)C)C)=O)(C(F)(F)F)C#CC3CC3)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution containing (±) 6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (12.97 g, 0.041 mol), 4-dimethylaminopyridine (1.02 g, 0.0083 mol), and (-) camphanic acid chloride (14.22 g, 0.06556 mol) in 350 mL of dry dichloromethane, stirred under argon in an ice bath, was added triethylamine (22.84 mL, 0.164 mol). The cooling bath was removed and the reaction was allowed to proceed at room temperature. After 75 min. the reaction was judged complete by thin layer chromatography (SiO2, 4% EtOAc in CHCl3), and the solution was diluted with 500 mL of CHCl3 then washed with 10% citric acid (2×), water (1×), and brine (1×). Drying (MgSO4), filtration, and removal of the solvent in vacuo left a colorless foam. This material was triturated with 200 mL of boiling hexane. On cooling to room temperature the desired diastereomeric camphanate imide precipitated. The solid was collected on a frit, washed with a little cold hexanes and dried in vacuo to give 7.79 g of 6-chloro-1-(1S)-camphanoyl-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one as white crystals. |
Here is a chemical reaction formula: Reactants are m3:C(C)O, amount is: 0.0 ;m1:Cl.NC(C(C(Cl)Cl)=O)(CC)C, amount is: 0.0 ;m2:C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:C(C)(=O)OCC, amount is: 0.0 ,Catalysts are m5:[Pd], amount is: 0.0 .Products are 0:Cl.NC(C(CCl)=O)(CC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a 2 l Parr bottle were placed 41 g of 3-amino-1,1-dichloro-3-methyl-2-pentanone hydrochloride, 0.8 g of 10% palladium over charcoal and 400 ml of ethanol (200 proof). The resulting mixture was shaken in a Parr apparatus at 50 psi for 3 hours. The crude reaction mixture was filtered through Celite® filter agent and evaporated in vacuo. A viscous oil resulted, which was taken up in approximately 400 ml of ethyl acetate and stirred at room temperature for several hours. The expected 3-amino-1-chloro-3-methyl-2-pentanone hydrochloride crystallized as a white solid. To the resulting suspension were added 300 ml of hexane. Filtration yielded 34 g (98%) of the expected 3-amino-1-chloro-3-methyl-2-pentanone hydrochloride. |
Here is a chemical reaction formula: Reactants are m2:CC(C([O-])([O-])[O-])(C)C, amount is: 0.0 ;m1:NC1=C(C=C(C(=O)OC)C=C1)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CO, amount is: 0.0 ,Catalysts are m3:S(O)(O)(=O)=O, amount is: 0.0 .Products are 0:CC=1OC2=C(N1)C=CC(=C2)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a 50 ml round-bottomed three-necked flask equipped with a 12-inch Vigraux column and a Dean Stark trap assembly were placed methyl 4-amino-3-hydroxybenzoate (10.0 g, 60 mmole), trimethylorthoacetate (10.8 g, 90 mmole), and concentrated sulfuric acid (0.25 g, 2.6 mmole). The resulting well-stirred mixture was heated at 115° C. until approximately 8 ml of methanol were collected in the Dean Stark trap. The reaction mixture was heated at 160° C. for another 60 minutes. The reaction mixture was cooled to room temperature and dissolved in ethyl acetate. The resulting organic solution was extracted sequentially with saturated aqueous sodium bicarbonate (1×100 ml), water (2×50 ml), brine, and dried over anhydrous magnesium sulfate. The solvent was removed in the rotary evaporator yielding 7.1 g of the expected methyl 2-methylbenzoxazole-6 carboxylate used as such in the next step. |
Here is a chemical reaction formula: Reactants are m3:CO, amount is: 0.0 ;m1:OC=1C=C(C(=O)O)C=CC1[N+](=O)[O-], amount is: 0.0 ;m2:Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:OC=1C=C(C(=O)OC)C=CC1[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a 1 liter round-bottomed flask were placed 25 g (0.14 mole) 3-hydroxy-4-nitrobenzoic acid, 37% hydrochloric acid (37 ml) and methanol (300 ml). The resulting mixture was refluxed for 10 hours. The reaction mixture was cooled to room temperature and the solvent eliminated in a rotary evaporator. The resulting residue was dissolved in ethyl acetate and washed sequentially with water (1×100 ml), aqueous sodium bicarbonate (1×100 ml), water (1×100 ml) and brine (1×100 ml). The organic layer was dried over anhydrous magnesium sulfate and solvent was removed in the rotary evaporator, yielding 22.5 g of the expected methyl 3-hydroxy-4-nitrobenzoate as a yellow solid which was used as such in the next step. |
Here is a chemical reaction formula: Reactants are m2:[OH-].[Na+], amount is: 0.0 ;m3:CO, amount is: 0.0 ;m5_m6:O, amount is: 0.0 MOLE;m4:O, amount is: 0.0 ;m1:NC1=C(C=C(C(=O)OC)C=C1Cl)OS(=O)(=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m6:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:NC1=C(C=C(C(=O)O)C=C1Cl)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a 2-liter round-bottomed flask were placed methyl 4-amino-5-chloro-3-methylsulfonyloxybenzoate (8.7 g, 31.1 mmole), 50% aqueous sodium hydroxide (10.1 g, 126 mmole), methanol (250 ml) and water (550 ml). The resulting mixture was refluxed for 3 hours. The reaction mixture was cooled down to room temperature and poured into a mixture of water and ethyl acetate. The aqueous layer was separated, neutralized to pH 6 with concentrated aqueous hydrochloric acid, and extracted with ethyl acetate (3×400 ml). The combined organic layers were washed with water (2×200 ml), dried over anhydrous magnesium sulfate and the solvent eliminated in the rotary evaporator yielding 4.3 g of the expected 4-amino-5-chloro-3-hydroxybenzoic acid (intermediate XII). (1H-NMR, DMSO-d6 12.5(1,bs); 10(1,bs); 7.22(1,s); 5.4(2,s)) |
Here is a chemical reaction formula: Reactants are m3:CO, amount is: 0.0 ;m2:[OH-].[Na+], amount is: 0.0 ;m1:O1CC(NC2=C1C=CC(=C2)C(=O)OC)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:O1CC(NC2=C1C=CC(=C2)C(=O)O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a 250 ml round-bottomed flask were place the preceding methyl 1,4-benzoxazine-3-one-6-carboxylate (5.8 g, 28 mmole), 50% aqueous sodium hydroxide (9.0 g, 112 mmole), methanol (125 ml), and water (19 ml). The resulting mixture was refluxed for 4 hours. The reaction mixture was cooled to room temperature and the solvent eliminated in the rotary evaporator. The crude reaction product was taken up in water and the resulting aqueous solution was washed with hexane (2×50 ml) and acidified to pH=1 with concentrated aqueous hydrochloric acid. The solid which formed was separated by suction filtration, and dried in a vacuum oven yielding 5.1 g of the expected 1,4-benzoxazine-3-one-6-carboxylic acid. |
Here is a chemical reaction formula: Reactants are m3_m5:C[C@H](CCCC(C)C)[C@H]1CCC2[C@@]1(CCC3C2CC=C4[C@@]3(CCC(C4)OC(=O)Cl)C)C, amount is: 0.0 ;m1_m2_m4:S(=O)(=O)(O)O.NC(NCCCCN)=N, amount is: 0.0 ;m1_m2_m4:[OH-].C[N+](C)(C)C, amount is: 0.0 ;m1_m2_m4:CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)O.C(=O)(O)CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Agmatine sulfate (100 mg, 0.438 mmol) was treated by tetramethylamonium hydroxide (158 mg, 0.876 mmol) in methanol (15 ml) for 1 h. The solvent was removed under reduced pressure. A suspension solution of the residue and cholesteryl chloroformate (197 mg, 0.438 mmol) in DMF (15 ml) was stirred at room temperature for 3 days. Filtration of the reaction mixture gave the crude product as a light yellow solid, which was purified by a silica gel column using chloroform-methanol-acetic acid (10:2:1) as eluent to yield the agmatinyl carboxycholesterol acetic acid salt as a white solid. 1H NMR (300 MHz, CD3OD): δ5.27 (broad s, 1 H), 4.65 (broad m, 1 H), 3.06 (t, 2 H), 2.99 (t, 2 H), 2.21 (broad d, 2 H), 1.95-0.65 (m, 31 H), 1.80 (s, 4 H), 0.91 (s, 3 H), 0.82 (d, 3 H), 0.76 (s, 3 H), 0.74 (s, 3 H), 0.59 (s, 3 H). LSIMS (NBA): m/e 543.4 for M+(C33H59N4O2). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C[N+](C)(C)CC(CC(=O)O)O.[Cl-], amount is: 0.0 ;m1_m2_m3:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC(C[N+](C)(C)C)CC([O-])=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of DL-carnitine hydrochloride (1.0 g, 5.05 mmol) and sodium hydroxide (0.303 g, 7.58 mmol) in ethanol (15 ml) was stirred at room temperature for 2 h. The formed white precipitate (NaCl) was removed by filtration, and the solvent was evaporated under reduced pressure to give a white solid, carnitine inner salt. A suspension of the carnitine inner salt and 1 -iodooctadecane (2.31 g, 6.06 mmol) in DMF-dioxane (3:5, 40 ml) was heated with an oil-bath at 120° C. under Ar2 for 4 h. The solvent was removed by rotavapor and vacuum, and the residue was chromatographied with silica gel column using CH3OH--CH3Cl as eluant to give 2.22 g (81%) of stearyl carnitine ester as a white solid: 1H NMR (CDCl3) δ4.79 (m, 1 H), 4.43 (d, J=5.3, 1 H), 4.09 (t, J=6.9, 2 H), 4.03 (d, J=13.0, 1 H), 3.67 (dd, J=10.3, 13.3, 1 H), 3.51 (s, 9 H), 2.79 (dd, J=5.7, 17.0, 1 H), 2.66 (dd, J=7.0, 17.1, 1 H), 1.80-1.60 (m, 4 H), 1.26 (broad s, 28 H), 0.88 (t, J=6.6, 3 H). LSIMS (NBA): m/e 414.4 for C25H52NO3 (cation). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C[N+](C)(C)CC(CC(=O)O)O.[Cl-], amount is: 0.0 ;m1_m2_m3:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC(C[N+](C)(C)C)CC([O-])=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of DL-carnitine hydrochloride (1.0 g, 5.05 mmol) and sodium hydroxide (0.303 g, 7.58 mmol) in ethanol (15 ml) was stirred at room temperature for 2 h. The formed white precipitate (NaCl) was removed by filtration, and the solvent was evaporated under reduced pressure to give a white solid, carnitine inner salt. A suspension of the carnitine inner salt and 1-iodooctadecane (2.31 g, 6.06 mmol) in DMF-dioxane (3:5, 40 ml) was heated with an oil-bath at 120° C. under argon for 4 h. The solvent was removed under reduced pressure, and the residue was purified by a silica gel column using CH3OH--CH3Cl (v/v, 0-10%) as eluent to give the stearyl carnitine ester as a white solid. A solution of a fresh prepared stearic anhydride (1.94 g, 3.52 mmol), stearyl carnitine ester (0.953 g, 1.76 mmol) and 4-dimethylaminopyridine (0.429 g, 3.52 mmol) in CH3Cl (dry, 15 ml) was stirred at room temperature under argon for four days. The solvent was removed under reduced pressure, and the residue was washed twice by cold diethyl ether. The solid was chromatographied on a silica gel column using MeOH--CHCl3 (v/v, 1:5) as eluent to give the stearyl stearoyl carnitine ester iodide. The iodide was exchanged by chloride with an anion exchange column to give the stearyl stearoyl carnitine ester chloride as a white solid. 1H NMR (300 MHz, CDCl3) δ5.67 (q, 1 H), 4.32 (d, 1 H), 4.07 (m, 3 H), 3.51 (s, 9 H), 2.82 (t, 2 H), 2.33 (t, 2 H), 1.59 (broad m, 4 H), 1.25 (broad s, 58 H), 0.88 (t, 6 H). LSIMS (NBA): m/e 680.6 for M+ (C43H86NO4). Anal. Calcd for C43H86 ClNO4.H2O: C, 70.30; H, 12.07; N, 1.91. Found: C, 70.08; H, 12.24; N, 1.75. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:[N+](=O)([O-])C=1C=C(C(=O)O)C=C(C1)C(F)(F)F, amount is: 0.0 ;m1_m3_m2:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(Cl)Cl, amount is: 0.0 ,Catalysts are m4:CN(C)C=O, amount is: 0.0 MOLE.Products are 0:C(C)OC(=O)C=1C=C(N)C=C(C1)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-nitro-5-trifluoromethylbenzoic acid (0.36 g, 1.53 mmol) in CH2Cl2 (20 mL) was added oxalyl chloride (0.58 g, 4.60 mmol) followed by DMF (3 drops). An immediate evolution of gas occurred and the reaction was stirred for 18 h. The solvent was removed under reduced pressure, the resulting oil was dissolved in THF (80 mL) and cooled to 0° C. To the cooled solution was added EtOH (5 mL) in THF (15 mL) and the mixture was stirred for 18 h at room temperature. The mixture was concentrated to remove the THF and the resulting precipitate was filtered and dried. The solid was dissolved in EtOH (25 mL) and 10% Pd/C (0.12 g) was added and the suspension was stirred for 15 h under a blanket of H2. The reaction was filtered through celite and the filtrate evaporated to dryness to provide 3-ethoxycarbonyl-5-trifluoromethylaniline as a yellow oil. This compound was then coupled to 2-chloro-4-trifluoromethyl pyrimidine-5-carbonyl chloride as described above to provide the title compound in a 12% yield; m.p. 67°-71° C. |
Here is a chemical reaction formula: Reactants are m4:[BH3-]C#N.[Na+], amount is: 0.0 ;m1_m2_m3_m5:C(C1=CC=CC=C1)=O, amount is: 0.0 ;m1_m2_m3_m5:ClC=1C=C(N)C=C(C1)Cl, amount is: 0.0 ;m1_m2_m3_m5:CC(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)NC1=CC(=CC(=C1)Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of benzaldehyde (1.04 g, 9.40 mmol), 3,5-dichloroaniline (1.71 g, 10.60 mmol), and HOAc (0.20 mL) in MeOH (35 mL) was cooled to 0° C. Then a solution of NaBH3CN (28.0 mL, 28.0 mmol, 1.0 M solution in THF) was added dropwise via a syringe pump over 0.25 h. The solution was allowed to stir an additional 0.3 h at 0° C., and then room temperature for 18 h. The excess NaBH3CN was quenched with HCl and the solvent was removed under reduced pressure. The resulting oil was dissolved in EtOAc/H2O, basified with NaOH, and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and the solvent removed under reduced pressure. The resulting oil was purified by chromatography (SiO2, 15:1 hexanes/EtOAc) to provide N-benzyl-3,5-dichloroaniline as a white solid. This compound was coupled to 2-chloro-4-trifluoromethylpyrimidine-5-carbonyl chloride as described and purified by chromatography (SiO2, 9:1 hexanes/EtOAc) to provide the title compound (15% yield) as a white foam; m.p. 102°-104° C. |
Here is a chemical reaction formula: Reactants are m1_m2:OC1=NC=C(C(=N1)C)C(=O)OCC, amount is: 0.0 ;m1_m2:O=P(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC1=NC=C(C(=N1)C)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of ethyl 2-hydroxy-4-methylpyrimidine-5-carboxylate (5 g, 27.5 mmol) and POCl3 (84 g, 550 mmol) was heated at reflux under N2 for 1 h. The reaction was cooled and concentrated. The residue was partitioned between CHCl3 and H2O and the organic layer was dried (Na2SO4), filtered, and concentrated to yield the title compound in a yield of 27% (1.5 g); 1HNMR (CDCl3) δ 9.04 (s, 1H), 4.42 (q, 2H), 2.85 (s, 3H), 1.43 (t, 3H). |
Here is a chemical reaction formula: Reactants are m1_m2_m4:ClC1=NC=C(C(=N1)C)C(=O)OCC, amount is: 0.0 ;m1_m2_m4:[OH-].[Na+], amount is: 0.0 ;m3:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=NC=C(C(=N1)C)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of ethyl 2-chloro-4-methylpyrimidine-5-carboxylate (1.0 g, 5 mmol), NaOH (0.24 g, 6 mmol) in H2O (30 mL) was stirred at room temperature for 3 h. The solution was acidified with 6N HCl and the resulting solid was filtered and dried to give the title compound (0.67 g 78%), 1HNMR (DMSO-d6) δ 9.01 (s, 1H), 2.75 (s, 3H). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=NC=C(C(=N1)C)C(=O)O, amount is: 0.0 ;m1_m2_m3_m4:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:ClCl, amount is: 0.0 ,Catalysts are m1_m2_m3_m4:CN(C)C=O, amount is: 0.0 MOLE.Products are 0:ClC1=NC=C(C(=N1)C)C(=O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-chloro-4-methylpyrimidine-5-carboxylic acid (0.81 g, 4.70 mmol), oxalyl chloride (0.89 g, 7.05 mmol), DMF (2 drops) in CH2 Cl2 (23 mL) was stirred at room temperature under N2 for 4 h. The solution was concentrated and distilled to give the title compound (0.55 g, 61%); b.p. 90°-100° C., 1.3 mm/Hg; 1HNMR (CDCl3) δ d 9.02 (s, 1H), 2.74 (s, 3H). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)OC=C(C(=O)OCC)C(=O)C(F)(F)F, amount is: 0.0 ;m1_m2_m3:FC(C(=N)N)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:CCO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)OC(=O)C=1C(=NC(=NC1)C(F)(F)F)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of ethyl ethoxymethylene-4,4,4-trifluoroacetoacetate (15 g, 62.5 mmol) and trifluoroacetamidine (12.6 g, 112.5 mmol) in EtOH (50 mL) was heated at reflux for 24 h under N2. The reaction mixture was cooled and concentrated. Chromatography (SiO2, 20% EtOAc/hexane) afforded ethyl-2,4-bis (trifluoromethyl)pyrimidine-5-carboxylate as an oil (7.0 g, 39%), 1HNMR (CDCl3) δ 9.37 (s, 1H), 3.70 (q, 2H), 1.27 (t, 3H). |
Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 MOLE;m1_m2_m4_m5:C(C)OC(=O)C=1C(=NC(=NC1)C(F)(F)F)C(F)(F)F, amount is: 0.0 ;m1_m2_m4_m5:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m5:CCO, amount is: 0.0 ;m1_m2_m4_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(C1=NC=C(C(=N1)C(F)(F)F)C(=O)O)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of ethyl-2,4-bis(trifluoromethyl)pyrimidine-5-carboxylate (5.0 g, 17 mmol) and NaOH (0.72 g, 18 mmol) in EtOH (20 mL) and H2O (50 mL) was stirred at room temperature for 1 h. The solution was acidified (HCl) and the resulting solid was filtered and dried to give 2,4-bis (trifluoromethyl)-pyrimidine-5-carboxylic acid (1.5 g, 25%), m.p. 59° C., 1HNMR (DMSO-d6) δ 9.62 (s, 1H). |
Here is a chemical reaction formula: Reactants are m1_m2:ClC1=NC=C(C(=N1)C(F)(F)F)C(=O)Cl, amount is: 0.0 ;m1_m2:O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC1=NC=C(C(=N1)C(F)(F)F)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-chloro-4-trifluoromethylpyrimidine-5-carbonyl chloride (2.1 g, 8.6 mmol) in H2O (10 mL) was stirred at 0° C. under N2 for 0.5 h. The resulting solid was filtered and dried to give the title compound (1.91 g, 98% yield); m.p. 232°-234° C. (dec.). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(#N)C1=NC=C(C(=N1)C(F)(F)F)C(=O)O, amount is: 0.0 ;m1_m2_m3_m4:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:ClCl, amount is: 0.0 ,Catalysts are m1_m2_m3_m4:CN(C)C=O, amount is: 0.0 MOLE.Products are 0:C(#N)C1=NC=C(C(=N1)C(F)(F)F)C(=O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-cyano-4-trifluoromethylpyrimidine-5-carboxylic acid (2.0 g, 9.2 mmol), oxalyl chloride (1.4 g, 11 mmol) and DMF (4 drops) in CH2 Cl2 (46 mL) was stirred at room temperature under N2 for 0.75 h. The reaction was concentrated and distilled (b.p. 100° C., 1.5 mm/Hg) to give the title compound (1.8 g, 82% yield); 1HNMR (CDCl3) δ 9.49 (s, 1H). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:CCOC(=O)/C(=C/N(C)C)/C=O, amount is: 0.0 ;m1_m2_m3_m4:Cl.C(C1=CC=CC=C1)(=N)N, amount is: 0.0 ;m1_m2_m3_m4:[Na], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CCO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)C1=NC=C(C=N1)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of ethyl 3-N,N-dimethylamino-2-formylacrylate (4.0 g, 23 mmol) (Arnold, Coll. Czech. Chem. Commun. 26:3051, 1961), benzamidine hydrochloride (4.0 g, 26 mmol) and sodium (0.65 g, 28 mmol) in EtOH (40 mL) was heated at reflux for 1 h. The solution was filtered and concentrated and the residue partitioned between EtOAc and dilute HCl (10%). The organic layer was dried (Na2SO4), and concentrated to give ethyl 2-phenylpyrimidine-5-carboxylate (4.0 g, 75% yield); m.p. >220° C. (dec.). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(C)OC=C(C(=O)OCC)C(=O)OCC, amount is: 0.0 ;m1_m2_m3_m4:FC(C(=N)N)(F)F, amount is: 0.0 ;m1_m2_m3_m4:CC[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CCO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(C1=NC=C(C(=N1)O)C(=O)OCC)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of diethyl ethoxymethylenemalonate (35.0 g, 162 mmol), trifluoroacetamidine (18 g, 162 mmol) and NaOEt (11.0 g, 162 mmol) in EtOH (200 mL) was heated at reflux for 6 h. The reaction mixture was concentrated and H2O (48 mL) was added. The resulting solid was filtered, washed with Et2O (300 mL) and H2O (200 mL), and dried to give the title compound (21 g, 50% yield); m.p. >220° C. (dec.); 1HNMR (DMSO-d6) δ 8.38, 4.16 (q, 2H), 1.25 (q, 3H). |
Here is a chemical reaction formula: Reactants are m1_m2_m4:FC(C1=NC=C(C(=N1)O)C(=O)OCC)(F)F, amount is: 0.0 ;m1_m2_m4:[OH-].[Na+], amount is: 0.0 ;m3:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(C1=NC=C(C(=N1)O)C(=O)O)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of ethyl 2-trifluoromethyl-4-hydroxypyrimidine-5-carboxylate (5.00 g, 19.4 mmol) and NaOH (0.93 g, 23.3 mmol) in H2O (20 mL) was stirred at 60° C. for 15 h. The reaction was acidified (conc. HCl) and concentrated until a solid began to form. The solid was filtered and dried to give 2-trifluoromethyl-4-hydroxypyrimidine-5-carboxylic acid (2.1 g, 53% yield); 1HNMR (DMSO-d6) δ 8.83 (s, 1H). |
Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 MOLE;m1_m2_m4_m5:OC1=NC=C(C(=N1)C(C(F)(F)F)(F)F)C(=O)OCC, amount is: 0.0 ;m1_m2_m4_m5:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m5:CCO, amount is: 0.0 ;m1_m2_m4_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC1=NC=C(C(=N1)C(C(F)(F)F)(F)F)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of ethyl 2-hydroxy-4-pentafluoroethylpyrimidine-5-carboxylate (4.0 g, 13 mmol) and NaOH (1.60 g, 39 mmol) in EtOH (20 mL) and H2O (45 mL) was heated at reflux for 1 h. The solution was cooled and acidified (conc. HCl). The resulting solid was filtered and dried to provide 2-hydroxy-4-pentafluoroethylpyrimidine-5-carboxylic acid (3.3 g, 98% yield); 1H-NMR (DMSO-d6) δ 9.90 (bs, 1H), 8.43 (s, 1H). |
Here is a chemical reaction formula: Reactants are m2:FC(C=1C=C(CN)C=C(C1)C(F)(F)F)(F)F, amount is: 0.0 ;m1:ClC1=NC=C(C(=N1)Cl)C(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC1=NC=C(C(=N1)Cl)C(=O)NCC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared as described in Example 1, but employing 2,4-dichloropyrimidine-5-carbonylchloride (0.10 g, 0.40 mmol) and 3,5-bistrifluoromethylbenzylamine (0.10 g, 0.45 mmol) to give the compound in a 61% yield (0.12 g); m.p. 144°-145° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:CC=1C(NC=C(N1)C(=O)OC)=O, amount is: 0.0 MOLE;m1_m3_m2:O=P(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1N=CC(=NC1C)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of methyl 4,5-dihydro-6-methyl-5-oxo-2-pyrazine carboxylate (M. Mano, T. Seo, K. Imai, Chem. Pharm. Bull 10:3057-3063, 1980) in DMF (20 mL) was added POCl3 (20 mL). The reaction was refluxed for 0.5 h and then poured into ice. The aqueous layer was extracted with CHCl3 dried (MgSO4) and concentrated. The residue was chromatographed (SiO2, CHCl3) to provide the title compound (2.34 g, 52% yield); m.p. 49°-50° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC=1N=CC(=NC1C)C(=O)OC, amount is: 0.0 ;m1_m2_m3:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1N=CC(=NC1C)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of methyl 5-chloro-6-methyl-2-pyrazine carboxylate (0.16 g, 0.86 mmol), K2CO3 (0.31 g, 2.18 mmol) and H2O was stirred for 2 h at room temperature. The reaction was filtered and acidified (20% HCl), and the resulting solid collected to provide the title compound (0.057 g, 39% yield); m.p. 116°-117° C. |
Here is a chemical reaction formula: Reactants are m2:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ;m1:FC1=NC=C(C(=N1)C(F)(F)F)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:ClCl, amount is: 0.0 ,Catalysts are m3:CN(C)C=O, amount is: 0.0 MOLE.Products are 0:FC1=NC=C(C(=N1)C(F)(F)F)C(=O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared as described in Example 25, but employing a solution of 2-fluoro-4-trifluoromethylpyrimidine-5-carboxylic acid (1.5 g, 7.1 mmol) and oxalyl chloride (1.0 g, 8 mmol), DMF (2 drops) in CH2 Cl2 (30 mL) resulted in a 75% yield (1.2 g); 1H NMR (CDCl3) δ 9.42 (s, 1H). |
Here is a chemical reaction formula: Reactants are m1:ClC1=NC=C(C(=N1)C(F)(F)F)C(=O)O, amount is: 0.0 ;m2:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=NC=C(C(=N1)C(F)(F)F)C(=O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared as described in Example 25, but employing a solution of 2-chloro-4-trifluoromethylpyrimidine-5-carboxylic acid (1.5 g, 7.1 mmol) and oxalyl chloride (1.0 g, 8 mmol) in CH2Cl2 (30 mL) resulted in a 70% yield (1.1 g); 1H NMR (CDCl3) δ 9.31 (s, 1H). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:[OH-].[Li+], amount is: 0.0 ;m1_m2_m3:C(C)(C)(C)OC(=O)NC(C(=O)OC)CN(CC1=CC(=C(C=C1)Cl)Cl)C(=O)OCC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:Cl, amount is: 0.0 ;m1_m2_m3:O1CCCC1.O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC(=O)NC(C(=O)O)CN(CC1=CC(=C(C=C1)Cl)Cl)C(=O)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Lithium hydroxide (62.4 mg) was added to a solution of the product of step (b) (1.0 g) in tetrahydrofuran/water (30 ml). The resulting solution was stirred at room temperature for 4 hours, diluted with 1N HCl (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colourless foam (990 mg). NMR δH (360 MHz, CDCl3) 1.44 (9H, s), 3,49 (2H, m), 4.51 (3H, m), 5.17 (2H, m), 5.79 (1H, br s), 7.20-7.42 (8H, m). m/e (CI+) 497 (MH+). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m6_m5:C(#N)[BH3-].[Na+], amount is: 0.0 ;m1_m2_m3_m6_m5:C=O, amount is: 0.0 ;m1_m2_m3_m6_m5:C(C)(C)(C)OC(=O)NC(C(=O)OC)CNCC1=CC(=C(C=C1)Cl)Cl, amount is: 0.0 ;m4:C(O)([O-])=O.[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m6_m5:C(C)#N, amount is: 0.0 MOLE;m1_m2_m3_m6_m5:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC(=O)NC(C(=O)OC)CN(C)CC1=CC(=C(C=C1)Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium cyanoborohydride (121 mg) was added to a solution of formaldehyde (570 mg), methyl 2-(tert-butoxycarbonylamino)-3-(3,4-dichlorobenzylamino)propionate (720 mg) and acetic acid (0.1 ml) in acetonitrile and the mixture was stirred at room temperature for 30 minutes. Aqueous sodium hydrogen carbonate (10 ml) was added and the mixture was extracted with ethyl acetate (3×20 ml). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colourless oil (722 mg). NMR δH (360 MHz, CDCl3) 1.45 (9H, s), 2.21 (3H, s), 2.73 (2H, d, J=7.0 Hz), 3.46 (2H, m), 3.75 (3H, s) 4.37 (1H, m), 5.19 (1H, br s), 7.10 (1H, dd, J=11.0 and 1.0 Hz), 7.36 (2H, m). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:[OH-].[Li+], amount is: 0.0 ;m1_m2_m3:C(C)(C)(C)OC(=O)NC(C(=O)OC)CN(C)CC1=CC(=C(C=C1)Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:Cl, amount is: 0.0 ;m1_m2_m3:O1CCCC1.O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC(=O)NC(C(=O)O)CN(C)CC1=CC(=C(C=C1)Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Lithium hydroxide (55 mg) was added to a solution of the product of step (a) (722 mg) in tetrahydrofuran/water (30 ml). The mixture was stirred at room temperature for 4 hours, diluted with hydrochloric acid (1M, 50 ml) and extracted with ethyl acetate (3×50 ml). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colourless foam (301 mg). NMR δH (250 MHz, CDCl3) 1.43 (9H, s), 2.59 (3H, s), 2.90 (1H, m), 3.22 (1H, m), 3.77 (1H, m) 4.10 (1H, m), 4.26 (1H, m),5.67 (1H, br s) 7.24 (1H, dd, J=11.0 and 1.0 Hz), 7.68 (2H,m). m/e (CI+) 377 (MH+). |
Here is a chemical reaction formula: Reactants are m1_m2_m5:ClC=1C=C(C=CC1Cl)CCBr, amount is: 0.0 ;m1_m2_m5:[Mg], amount is: 0.0 ;m4:Cl, amount is: 0.0 ;m3_m6:C(C(=O)OCC)(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:CCOCC, amount is: 0.0 ;m3_m6:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=C(C=CC1Cl)CCC(C(=O)OCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(3,4-Dichlorophenyl)ethyl bromide (5 g, 19.7 mmol) was added slowly to a suspension of magnesium turnings (0.48 g, 19.7 mmol) in ether (30 ml). After spontaneous reflux had finished the mixture was stirred under reflux for 15 minutes and allowed to cool to room temperature. The mixture was added dropwise via cannula to a stirred, cooled (-25° C.) solution of diethyl oxalate (3 g, 20.7 mmol) in THF (15 ml). The mixture was stirred at -10° C. for 30 minutes and allowed to warm to room temperature. Hydrochloric acid (2M, 15 ml) was added and the mixture was extracted with ether (2×20 ml). The combined organic fractions were washed with water, dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/hexane (10:90) to give the title compound (0.7 g). |
Here is a chemical reaction formula: Reactants are m2_m3_m4_m5:ClC=1C=C(C=CC1Cl)CCC(C(=O)OCC)=O, amount is: 0.0 ;m2_m3_m4_m5:C(C1=CC=CC=C1)N, amount is: 0.0 ;m2_m3_m4_m5:C(#N)[BH3-].[Na+], amount is: 0.0 ;m1:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3_m4_m5:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)NC(C(=O)OCC)CCC1=CC(=C(C=C1)Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of acetic acid (0.29 ml, 5 mmol), the product of step (a) (700 mg, 2.5 mmol), benzylamine (0.56 ml, 5 mmol) and sodium cyanoborohydride (320 mg, 5 mmol) in ethanol (10 ml) was stirred at room temperature for 16 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and aqueous sodium carbonate (saturated). The organic layer was dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/hexane (10:90) to give the title compound as an oil (310 mg). m/e (CI+) 366 (MH+). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:[OH-].[Li+], amount is: 0.0 ;m1_m2_m3_m5:O, amount is: 0.0 ;m1_m2_m3_m5:C(C1=CC=CC=C1)N(C(C(=O)OCC)CCC1=CC(=C(C=C1)Cl)Cl)C(=O)OC(C)(C)C, amount is: 0.0 ;m4:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N(C(C(=O)O)CCC1=CC(=C(C=C1)Cl)Cl)C(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Lithium hydroxide (80 mg 1.8 mmol) and water (2 ml) were added to a solution of the product of step (c) (280 mg, 0.6 mmol) in THF (5 ml) and the mixture was stirred at room temperature for 16 hours. Acetic acid (0.5 ml) was added and the mixture was partitioned between ethyl acetate and water. The organic layer was dried (Na2SO4) and the solvent was evaporated under reduced pressure to give the title compound as a colourless foam (234 mg) m/e (CI+) 438 (MH+). |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)(=O)[O-].[NH4+], amount is: 0.0 ;m1_m2:C(#N)[BH3-].[Na+], amount is: 0.0 ;m3:ClC1=CC=C(OC(C(C)=O)C)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(OC(C(C)N)C)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 82 g of ammonium acetate and 6.7 g of sodium cyanoborohydride were added to a solution containing 21 g of 3-(4-chlorophenoxy)-2-butanone dissolved in 500 ml of methanol, and the reaction mixture was stirred for 20 hours at room temperature. After the reaction mixture was concentrated under reduced pressure, 180 ml of concentrated hydrochloric acid, 100 ml of water, and 300 ml of diethyl ether were added to the residue. The obtained water layer was alkalified using a 5% aqueous solution of sodium hydroxide, and then the organic substances were extracted with 500 ml of ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. A fraction possessing a low boiling point was removed from the obtained oily products to afford 18 g (yield 86%) of the desired product. |
Here is a chemical reaction formula: Reactants are m3:ClC1=NC=CC=N1, amount is: 0.0 ;m1_m2_m5:NC(CO)C, amount is: 0.0 ;m1_m2_m5:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CN(C=O)C, amount is: 0.0 MOLE;m1_m2_m5:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(COC1=NC=CC=N1)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2.0 g of 2-amino-1-propanol was added dropwise to a stirred mixture of 1.3 g of 60% sodium hydride and 30 ml of N,N-dimethylformamide at room temperature. After the reaction mixture was stirred for 30 minutes, a solution containing 3.7 g of 2-chloropyrimidine dissolved in N,N-dimethylformamide was added dropwise to the reaction mixture. The mixture was stirred for 2 hours at 100° C. After completion of the reaction, the reaction mixture was cooled. The solids in the reaction mixture were filtered off. The solvent in the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel to obtain 2.1 g of the desired product (yield: 50%). |
Here is a chemical reaction formula: Reactants are m1_m2_m4:NC(CO)C, amount is: 0.0 ;m1_m2_m4:[H-].[Na+], amount is: 0.0 ;m3:Cl.ClC1=CC=NC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(COC1=CC=NC=C1)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 6.2 g of 2-amino-1-propanol was added dropwise to a stirred mixture of 4.0 g of 60% sodium hydride and 50 ml of N,N-dimethylformamide at 5° C.~10° C. After the reaction mixture was stirred for 30 minutes, 12.5 g of 4-chloropyridine hydrochloride in limited amounts was added to the reaction mixture. The mixture was stirred for 20 hours at room temperature. After completion of the reaction, the solids in the reaction mixture were filtered off. The solvent in the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel to obtain 3.8 g of the desired product (yield: 30%). |
Here is a chemical reaction formula: Reactants are m3:ClC1=CC=C(C#N)C=C1, amount is: 0.0 ;m2:NC(CO)(C)C, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE;m1:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C1=CC=C(OCC(C)(C)N)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4.0 g of 60% sodium hydride was added to a solution containing 8.9 g of 2-amino-2-methyl-1-propanol dissolved in 100 ml of N,N-dimethylformamide in an ice bath. After the reaction mixture was stirred for 30 minutes at room temperature, 13.7 g of 4-chlorobenzonitrile was added to the reaction mixture and the reaction mixture was stirred for 15 hours at room temperature. The reaction mixture was poured into water. The organic layer of the reaction mixture was extracted with ethyl acetate, washed with water, and then dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure. The fraction possessing a low boiling point was removed from the residue, thus obtaining 15 g of the desired product (yield: 79%). |
Here is a chemical reaction formula: Reactants are m1:Cl, amount is: 0.0 MOLE;m2:N#N.C(C)(C)(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(COC1=CC=C(C=C1)C#N)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.C(#N)C1=CC=C(OCC(C)NC([C@@H](N)C(C)C)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Hydrogen chloride gas was introduced into a solution containing 3.7 g of N2 -tert-butoxycarbonyl-N1 -[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide dissolved in 100 ml of methylene chloride for 1 hour at room temperature. After the completion of the reaction, the methylene chloride was removed under reduced pressure, thus yielding a crude crystal. The crude crystal was washed with acetone to afford 3.1 g of the desired product (yield: 100%). |
Here is a chemical reaction formula: Reactants are m2:N#N.C(C)(C)(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(COC1=CC=C(C=C1)C#N)(C)C, amount is: 0.0 ;m1:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C1=CC=C(OCC(C)(C)NC([C@@H](N)C(C)C)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Hydrogen chloride gas was introduced into a solution containing 3.7 g of N2 -tert-butoxycarbonyl-N1 -[2-(4-cyanophenoxy)-1,1-dimethylethyl]-L-valinamide dissolved in 50 ml of methylene chloride for 3 hours at room temperature. After the completion of the reaction, the methylene chloride was removed under reduced pressure. A saturated aqueous solution of sodium bicarbonate was added to the residue. The organic layer in the residue was extracted with methylene chloride, washed with water, and then dried over anhydrous magnesium sulfate. The solvent in the organic layer was removed under reduced pressure, thus yielding 2.4 g of the desired product (yield: 87%). |
Here is a chemical reaction formula: Reactants are m1:CN1CCOCC1, amount is: 0.0 ;m2:Cl.C(#N)C1=CC=C(OCC(C)NC([C@@H](N)C(C)C)=O)C=C1, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE;m3:ClC(=O)OC1=CC(=CC=C1)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C1=CC=C(OCC(C)NC([C@@H](NC(=O)OC2=CC=CC=C2)C(C)C)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1.0 g of N-methylmorpholine was added to a solution containing 1.5 g of N1 -[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide hydrochloride dissolved in 100 ml of methylene chloride, at -20° C. After 0.9 g of 3-methoxyphenyl chloroformate was added to the mixture at -20° C., the reaction mixture was allowed to sit and warm naturally to room temperature while being stirred. The whole mixture was stirred for 2 hours at room temperature. Water was subsequently added to the reaction mixture. After the methylene chloride layer was washed with water, the organic layer was dried over anhydrous magnesium sulfate and the methylene chloride was removed under reduced pressure. The residue was purified by column chromatography on silica gel, thus yielding 0.25 g of the desired product in the form of a white plated crystal (yield: 12%). |
Here is a chemical reaction formula: Reactants are m3:ClC(=O)OCC(C)C, amount is: 0.0 ;m1:CN1CCCCC1, amount is: 0.0 ;m2:ClCCOC(=O)N[C@@H](C(C)C)C(=O)O, amount is: 0.0 ;m4:C(#N)C1=CC=C(OCC(C)N)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(Cl)Cl, amount is: 0.0 ;m6:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(#N)C1=CC=C(OCC(C)NC([C@@H](NC(=O)OC2=CC=CC=C2)C(C)C)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.5 g of N-methylpiperidine was added to a solution containing 1.1 g of N-(2-chloroethoxycarbonyl)-L-valine dissolved in 40 ml of methylene chloride, at -20° C. After the mixture was stirred for 15 minutes at the same temperature, 0.7 g of isobutyl chloroformate was added to the mixture at -40° C., and subsequently the whole mixture was stirred for 1 hour at -20° C. 0.9 g of 2-(4-cyanophenoxy)-1-methylethylamine was added to this mixture at -60° C., and then the reaction mixture was allowed to sit and warm naturally to room temperature while being stirred. The whole mixture was stirred for 20 hours at room temperature. Water was subsequently added to the reaction mixture. After the methylene chloride layer was washed successively with a 5% aqueous solution of sodium bicarbonate and water, the organic layer was dried over anhydrous magnesium sulfate and the methylene chloride was removed under reduced pressure. The residue, which was an oily substance, was purified by column chromatography on silica gel, thus yielding 1.0 g of the desired product in the form of colorless grains (yield: 52%). |
Here is a chemical reaction formula: Reactants are m2:C(#N)C1=CC=C(OCC(C)NC([C@@H](N)C(C)C)=O)C=C1, amount is: 0.0 ;m3:C1=CC=C(C=C1)OC(=S)Cl, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE;m1:CN1CCOCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C1=CC=C(OCC(C)NC([C@@H](NC(=O)OC2=CC=CC=C2)C(C)C)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.4 g of N-methylmorpholine was added to a suspension containing 1.1 g of N1 -[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide suspended in 40 ml of methylene chloride, at -15° C. After 0.7 g of phenyl chlorothionoformate was added to the mixture at -15° C., the reaction mixture was allowed to sit and warm naturally to room temperature while being stirred, and then the whole mixture was stirred for 15 hours at room temperature. Water was subsequently added to the reaction mixture. After the methylene chloride layer was washed with water, the organic layer was dried over anhydrous magnesium sulfate and the methylene chloride was removed under reduced pressure. The residue was purified by column chromatography on silica gel, thus yielding 1.2 g of the desired product in the form of a yellow glutinous substance (yield: 75%). |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 MOLE;m1:CN1CCOCC1, amount is: 0.0 ;m2:C(#N)C1=CC=C(OCC(C)NC([C@@H](N)C(C)C)=O)C=C1, amount is: 0.0 ;m3:ClC(=S)SC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C1=CC=C(OCC(C)NC([C@@H](NC(=O)OC2=CC=CC=C2)C(C)C)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.5 g of N-methylmorpholine was added to a suspension containing 1.4 g of N1 -[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide suspended in 40 ml of methylene chloride, at -15° C. After 0.9 g of phenyl chlorodithioformate was added to the mixture at -15° C., the reaction mixture was allowed to sit and warm naturally to room temperature while being stirred, and subsequently the whole mixture was stirred for 15 hours at room temperature. Water was subsequently added to the reaction mixture. After the methylene chloride layer was washed with water, the organic layer was dried over anhydrous magnesium sulfate and the methylene chloride was removed under reduced pressure. The residue was purified by column chromatography on silica gel, thus yielding 1.4 g of the desired product in the form of a yellow glutinous substance (yield: 66%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:N1=CC=C(C=C1)COC1=CC=C2CCCC(C2=C1)=O, amount is: 0.0 ;m1_m2_m3:C(C1=CC=CC=C1)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)NC1CCCC2=CC=C(C=C12)OCC1=CC=NC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of Compound 1 (820 mg, 3.24 mmol) and benzyl amine (354 L, 3.24 mmol) in benzene (10 mL) was heated to reflux under azeotropic conditions. After the calculated amount of water was collected, the reaction was cooled and concentrated in vacuo. The residue was taken-up into ethanol (5 mL) and added to a slurry of sodium boroydride (246 mg, 6.48 mmol) in ethanol (15 mL). The reaction was heated to 80° C., stirred for 30 min, cooled and concentrated in vacuo. The residue was diluted with ethyl acetate followed by the slow addition of 1N hydrochloric acid. The layers were separated. The aqueous phase was adjusted to pH 7 with 2N sodium hydroxide and extracted with methylene chloride (2×). The organics were combined, washed with brine, dried over anh. magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel (elution with 5% methanol:methylene chloride) provided 1.09 g of Compound 12 as an oil. |
Here is a chemical reaction formula: Reactants are m3:CO, amount is: 0.0 ;m2:[H][H], amount is: 0.0 MOLE;m1_m4:N1=CC=C(C=C1)COC1=CC=C2CCC(C(C2=C1)=O)=CC=1C=NC=CC1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m1_m4:[Pd], amount is: 0.0 .Products are 0:CC=1C(=C2CCC(C(C2=CC1OCCC)=O)CC=1C=NC=CC1)OCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of Compound 25 (3.96 g, 10.8 mmol) and 10% palladium on carbon (600 mg) in abs. methanol (100 mL) was hydrogenated at 1 atm for 12 hr. The hydrogen was replaced with nitrogen, the reaction was filtered and concentrated in vacuo. Chromatography of the residue on silica gel (elution with 20% ethyl acetate:hexanes) provided 2.72 g of Compound 26. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:NC=1C(=NC(=CC1)Cl)C(C(=O)OCC)C(=O)OCC, amount is: 0.0 MOLE;m1_m2_m3:NC=1C(=NC(=CC1)C(C(=O)OCC)C(=O)OCC)Cl, amount is: 0.0 MOLE;m1_m2_m3:C(CC(=O)OCC)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1N=C2CC(NC2=CC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The mixture containing 3-amino-2-bis(ethoxycarbonyl)methyl-6-chloropyridine, 3-amino-6-bis(ethoxycarbonyl)methyl-2-chloropyridine and diethyl malonate was taken up in 6N HCl solution (700 mL) and heated at reflux for 5 hours. After removing the aqueous acid in vacuo, the residue was taken up in water and again concentrated to yield 5-chloro-4-azaoxindole as a brown solid which was dried in the air. The yield was 7.04 g. (32% overall from 2,6-dichloro-3-nitropyridine). An analytical sample was prepared by recrystallization from isopropanol; m.p. 250°-254° C. (dec.). |
Here is a chemical reaction formula: Reactants are m1_m2:NC=1C(=NC=C(C1)Cl)C(C(=O)OCC)C(=O)OCC, amount is: 0.0 MOLE;m1_m2:Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC1=CN=C2CC(NC2=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3-amino-2-bis(ethoxycarbonyl)methyl-5-chloropyridine and 6N HCl (325 mL) was heated at reflux for 4 hours. After removing the aqueous acid in vacuo, the residue was taken up in water and filtered to remove a small amount of black insoluble material. On adjustment of the filtrate to pH 6.5 with solid NaHCO3, 6-chloro-4-azaoxindole precipitated as a tan solid (2.6 g) which was collected by filtration. The filtrate was extracted with ethyl acetate and the combined extracts were dried (MgSO4) and concentrated to yield an additional quantity of 6-chloro-4-azaoxindole (3.6 g). The total yield was thus 6.2 g (71% overall from 2,5-dichloro-3-nitropyridine). |
Here is a chemical reaction formula: Reactants are m4:C(C)(=O)O, amount is: 0.0 ;m5:Cl, amount is: 0.0 ;m1_m6_m2_m3_m7:CC(C)([O-])C.[K+], amount is: 0.0 ;m1_m6_m2_m3_m7:ClC1=NC=C(C=C1)[N+](=O)[O-], amount is: 0.0 ;m1_m6_m2_m3_m7:ClC1=CC=C(OCC#N)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6_m2_m3_m7:O1CCCC1, amount is: 0.0 ;m1_m6_m2_m3_m7:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(=N1)CC#N)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of potassium t-butoxide (24.69 g, 220 mmol, 2.2 eq) in anhydrous tetrahydrofuran (150 ml) at -50° C. under nitrogen, a solution of 2-chloro-5-nitropyridine (15.85 g, 100 mmol) and (4-chlorophenoxy)acetonitrile (E. Grochowski et al., Bull. Acad. Pol. Sci. Ser. Sci. Chim., 11, 443 (1963)) (18.44 g, 110 mmol, 1.1 eq) in anhydrous tetrahydrofuran (150 ml) was added dropwise at such a rate that the reaction temperature was maintained at -40° to -50° C. with cooling in a dry ice/acetone bath. The resultant purple colored reaction mixture was then stirred at -78° C. under nitrogen for 1 hour, at which time glacial acetic acid (20 ml, 0.35 mol, 3.5 eq) was added to the reaction, and the mixture was allowed to warm to room temperature. A solution of 5% HCl (100 ml) was added to the reaction mixture and this aqueous mixture was extracted with ethyl ether (100 ml) and then with methylene chloride (2×100 ml). The extracts were combined, dried over magnesium sulfate, and passed through a silica gel filter (approximately 150 g) followed by methylene chloride (1200 ml). This filtrate was evaporated under reduced pressure, and the residual oil was chromatographed using silica gel (approximately 300 g) and eluted with 25% hexanes in methylene chloride to afford an oil (Rf =0.52 in methylene chloride) which was triturated in cold anhydrous ether to afford 6-chloro-3-nitro-2-pyridyl acetonitrile (1.37 g, 7%) as a white crystalline solid: mp, 121.5°-123.5° C. Further elution yielded another oil (Rf =0.48 in methylene chloride) which was triturated with cold anhydrous ethyl ether to afford (2-chloro-5-nitro-4-pyridyl)acetonitrile (1.87 g, 9%) as a white crystalline solid, m.p. 87°-89° C. IR (KBr) 3080, 2240, 1600, 1545, 1520, 1450, 1390, 1340, 1135 cm-1. |
Here is a chemical reaction formula: Reactants are m2:C(=O)(O)[O-].[Na+], amount is: 0.0 MOLE;m1:NC=1C(=CC(=NC1)Cl)CC#N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=C2CC(NC2=CN1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (5-Amino-2-chloro-4-pyridyl)acetonitrile (1.40 g, 8.4 mmol) was taken up in 6N HCl solution (100 mL) and heated between 50° and 100° C. for 2 hours. After cooling, the solution was adjusted to pH 7 by addition of solid NaHCO3 and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was subjected to flash chromatography on silica gel using ethyl acetate as eluant. (Some methanol was used to help dissolve the solid). Fractions containing the desired product were combined and concentrated to leave the title compound as a solid (650 mg, 46%), m.p. 230° C. (dec.) The NMR spectrum indicated that this material contained a small amount of the by-product, 2-amino-5-chloro-6-azaindole in addition to the title compound. Nonetheless, this material was used in the next step without further purification. |
Here is a chemical reaction formula: Reactants are m1_m3_m4:BrC1(C(NC2=C(C=NC=C12)Br)=O)Br, amount is: 0.0 ;m2:[H][H], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3_m4:C(C)O, amount is: 0.0 ,Catalysts are m1_m3_m4:[Pd], amount is: 0.0 .Products are 0:N1C(CC2=CN=CC=C12)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3,3,7-tribromo-5-azaoxindole (6.4 g, 17.3 mmol) in ethanol (1200 ml) was added 10% Pd on charcoal (3.2 g). The mixture was hydrogenated under 3 atm. hydrogen gas for 3 hours using a Parr shaker. The catalyst was removed by filtration of the mixture through a pad of Celite®, washing well with ethanol. On removal of the solvent, a brown solid remained (predominantly the hydrobromide of the desired product), 3.5 g. This was dissolved in water, treated with activated charcoal and filtered through Celite®. The pH of the filtrate was adjusted to 7.5 by the addition of saturated aqueous NaHCO3 solution. The mixture was then extracted with n-butanol (3×). The combined n-butanol extracts were washed with brine, dried over magnesium sulfate and concentrated in vacuo to leave a solid. This was triturated with butanone and filtered to collect 5-azaoxindole as a tan solid (1.6 g, 69%). After removal of butanone, the mother liquor yielded a solid which was recrystallized from methanol to yield more of the title compound (50 mg), m.p.>250° C. |
Here is a chemical reaction formula: Reactants are m2:[Na], amount is: 0.0 MOLE;m4:S1C(=CC=C1)C(=O)OCC, amount is: 0.0 ;m3:N1C(CC2=CN=CC=C12)=O, amount is: 0.0 ;m1_m5:[Na], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CS1)C(=O)C1C(NC2=CC=NC=C12)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Pellets of sodium metal (1.15 g, 50 mmol) were added to dry ethanol (30 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, solid 5-azaoxindole (1.40 mg, 10.4 mmol) was added followed by ethyl 2-thiophenecarboxylate (2.7 mL, 20.1 mmol). The mixture was heated under nitrogen at reflux for 1 hour. At this point, the volume of the mixture was reduced 50% by distillation of ethanol at atmospheric pressure. The mixture was cooled and poured into ice/water. The resulting solution was filtered to remove a small amount of insoluble material which was washed well with water. Upon acidification of the filtrate to pH 7 with 6N HCl solution, the product precipitated. This was collected by filtration, washed with water and dried in the air to yield the title compound as a yellow/brown solid (2.0 g, 83%). |
Here is a chemical reaction formula: Reactants are m3_m4:NC=1C(=NC=C(C1)F)C(C(=O)OCC)C(=O)OCC, amount is: 0.0 MOLE;m3_m4:C(CC(=O)OCC)(=O)OCC, amount is: 0.0 MOLE;m1_m2:C(C)OC(=O)C(C1=NC=C(C=C1[N+](=O)[O-])F)C(=O)OCC, amount is: 0.0 MOLE;m1_m2:C(CC(=O)OCC)(=O)OCC, amount is: 0.0 MOLE;m5_m6:NC=1C(=NC=C(C1)F)C(C(=O)OCC)C(=O)OCC, amount is: 0.0 MOLE;m5_m6:C(CC(=O)OCC)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m8_m9:O, amount is: 0.0 ;m12:C(C)O, amount is: 0.0 MOLE;m10:C(C)O, amount is: 0.0 ;m11:Cl, amount is: 0.0 ;m7:C(C)O, amount is: 0.0 ,Catalysts are m8_m9:[Ni], amount is: 0.0 MOLE.Products are 0:FC1=CN=C2CC(NC2=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The mixture of 2-bis(ethoxycarbonyl)methyl-5-fluoro-3-nitropyridine and diethyl malonate was dissolved in ethanol (100 mL) and added to a suspension of 50% Raney nickel in water (7.8 g) diluted with ethanol (150 mL). The mixture was hydrogenated in a Parr shaker at 3 atmospheres pressure overnight and then filtered through diatomaceous earth (Celite (trademark)) to remove the catalyst. The solvent was removed in vacuo to leave a mixture of 3-amino-2-bis(ethoxycarbonyl)methyl-5-fluoropyridine and diethyl malonate as an oil. The mixture containing 3-amino-2-bis(ethoxycarbonyl)methyl-5-fluropyridine and diethyl malonate was taken up in 6N HCl solution (280 mL) and heated at reflux for 3 hours. After removing the aqueous acid in vacuo, the residue was taken up in water and again concentrated to leave a solid. This was taken up in dry ethanol and concentrated two times to obtain the title compound as a light green solid (4.07 g) which was triturated with hot ethyl acetate and dried in the air. Although somewhat impure by NMR this material was used in directly in the next step without further purification. |
Here is a chemical reaction formula: Reactants are m4:NC=1C(=NC(=C(C1)Cl)Cl)C(C(=O)OCC)C(=O)OCC, amount is: 0.0 ;m5:NC1(C(N=C(C=C1)Cl)C(C(=O)OCC)C(=O)OCC)Cl, amount is: 0.0 ;m1_m2_m3:C(C)OC(=O)C(C1=NC(=C(C=C1[N+](=O)[O-])Cl)Cl)C(=O)OCC, amount is: 0.0 MOLE;m1_m2_m3:C(C)OC(=O)C(C1=NC(=C(C=C1Cl)[N+](=O)[O-])Cl)C(=O)OCC, amount is: 0.0 MOLE;m1_m2_m3:C(C)C(C(=O)[O-])(C(=O)[O-])CC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6:C(C)O, amount is: 0.0 ;m9:C(C)O, amount is: 0.0 ;m7_m8:O, amount is: 0.0 ;m10:Cl, amount is: 0.0 ;m11:CCCCCC.C(C)(=O)OCC, amount is: 0.0 MOLE,Catalysts are m7_m8:[Ni], amount is: 0.0 MOLE.Products are 0:ClC=1N=C2CC(NC2=CC1Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The mixture of 2-bis(ethoxycarbonyl)methyl-5,6-dichloro-3-nitropyridine, 2-bis(ethoxycarbonyl)methyl-3,6-dichloro-5-nitropyridine and diethylmalonate was dissolved in ethanol (100 mL) and added to a suspension of 50% Raney nickel in water (30 g) diluted with ethanol (10 mL). The mixture was hydrogenated in a Parr shaker at 3 atmospheres pressure for 5 hours and then filtered through diatomaceous earth (Celite (trademark)) to remove the catalyst. The solvent was removed in vacuo to leave an oil which was subjected to flash chromatography on silica gel eluting with 4:1 hexane/ethyl acetate. Each of the fractions was separately concentrated and the residues examined by 1H NMR in deuterochloroform. Eluted after diethylmalonate was the desired product, 3-amino-2-bis(ethoxycarbonyl)methyl-5,6-dichloropyridine, followed closely thereafter by the unwanted isomer, 5-amino-2-bis(ethoxycarbonyl)methyl-3,6-dichloropyridine. Although clean separation from diethyl malonate was achieved, the bulk of the mass of desired product and the isomer eluted as mixed fractions. Leading fractions containing only 3-amino-2-bis(ethoxycarbonyl)methyl-5,6-dichloropyridine and mixed fractions containing at least 10% of this material were combined to afford a solid consisting of 3-amino-2-bis(ethoxycarbonyl)methyl-5,6-dichloropyridine (3.17 g) and the unwanted isomer, 3-amino-2-bis(ethoxycarbonyl)methyl-3,6-dichloropyridine (4.03 g). This mixture was taken up in 6N HCl solution (120 mL) and heated at reflux for 3 hours. After cooling to room temperature the volatiles were removed in vacuo. Ethanol was added and then evaporated to help remove water. This process was repeated. The resulting brown solid was subjected to flash chromatography on silica gel using 9:1 chloroform/methanol as eluant. All fractions containing the desired product were combined and concentrated to leave a solid which was triturated with methanol to afford 5,6-dichloro-4-azaoxindole (1.42 g, 71%) from 3-amino-2-bis(ethoxycarbonyl)methyl-5,6-dichloropyridine, 13% overall from 3-nitro-2,5,6-trichloropyridne). M.p. 230°-233° C. (dec). |
Here is a chemical reaction formula: Reactants are m2_m3:ClC1=CC=C(OCC#N)C=C1, amount is: 0.0 ;m2_m3:C(C)(C)OC1=NC=C(C=C1)[N+](=O)[O-], amount is: 0.0 MOLE;m4_m5:Cl, amount is: 0.0 MOLE;m4_m5:Cl, amount is: 0.0 ;m1_m6:CC(C)([O-])C.[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:CN(C=O)C, amount is: 0.0 ;m1_m6:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC=1C(=NC(=CC1)OC(C)C)CC#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of potassium-t-butoxide (12.34 g, 110 mmol) in dry dimethylformamide (DMF) (30 mL) cooled at -10° C. under a nitrogen atmosphere was added dropwise a solution of (4-chlorophenoxy)acetonitrile (9.22 g, 55 mmol) and 2-isopropoxy-5-nitro pyridine (prepared according to the methodology of Friedman, et al., J. Am. Chem. Soc. 69, 1204 (1947)) (9.11 g, 50 mmol) in DMF (30 mL). The resulting purple solution was maintained at 0° to 10° C. for 1 hour. Aqueous hydrochloric acid was added (80 mL, 5% HCl) and the resulting mixture was allowed to warm to room temperature. The mixture was extracted twice with methylene chloride. The combined extracts were dried (MgSO4) and concentrated in vacuo to leave an oil which was passed through a thick pad of silica gel, eluting with 1:1 methylene chloride/hexane. The filtrate was evaporated under reduced pressure and the residual oil containing the desired (6-isopropoxy-3-nitro-2-pyridyl) acetonitrile) was dissolved in a 6:1 mixture of ethanol and acetic acid (10 mL) to which was added 5% palladium/carbon (0.8 g). The mixture was hydrogenated on a Parr shaker at 3 atmospheres pressure for 5 hours. The catalyst was removed by filtration of the mixture through diatomaceous earth (Celite (trademark)) and The filtrate was concentrated in vacuo. The residual oil was taken up in water and the pH was adjusted to 10 by addition of sodium carbonate. The mixture was extracted twice with methylene chloride and the combined extracts were dried (MgSO4) and concentrated. The residue was subjected to flash chromatography on silica gel eluting successively with 1:2 ether/hexane, 1:1 ether/hexane and ethyl acetate. Fractions containing the product eluted with ethyl acetate were combined and evaporated to provide (3-amino-6-isopropoxy-2-pyridyl)acetonitrile as an off-white solid (5.60 g, 59%); m.p. 83°-85° C. |
Here is a chemical reaction formula: Reactants are m2:ClC1=CN=C2C(C(NC2=C1)=O)C(=O)C=1OC=CC1, amount is: 0.0 ;m0_m1:ClC1=CN=C2C(C(NC2=C1)=O)C(=O)C=1OC=CC1, amount is: 0.0 MOLE;m5:ClS(=O)(=O)NC=O, amount is: 0.0 MOLE;m4:C(C)#N, amount is: 0.0 ;m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m8_m7:C(C)(=O)O, amount is: 0.0 MOLE;m8_m7:O, amount is: 0.0 MOLE;m6:CS(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CN=C2C(C(N(C2=C1)C(=O)N)=O)C(=O)C=1OC=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 6-chloro-3-(2-furoyl)-4-azaoxindole (Example 12) according to the procedure of Example 2C, using 400 mg (1.5 mmol) 6-chloro-3-(2-furoyl)-4-azaoxindole, 0.19 ml (2.25 mmol) N-chlorosulfonyl isocyanate and 15 ml acetonitrile. The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO (5 ml), for 2 hours in a flask open to the air. The product was isolated by dilution with water filtration, and recrystallization from acetic acid. Yield: 160 mg (35%). |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)(=O)C1C(NC2=CC(=CN=C12)Cl)=O, amount is: 0.0 ;m0_m1:C(C1=CC=CC=C1)(=O)C1C(NC2=CC(=CN=C12)Cl)=O, amount is: 0.0 MOLE;m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)(=O)C1C(N(C2=CC(=CN=C12)Cl)C(=O)N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 3-benzoyl-6-chloro-4-azaoxindole (Example 14) according to the procedure of Example 2C, using 3-benzoyl-6-chloro-4-azaoxindole (500 mg, 1.83 mmol), N-chlorosulfonyl isocyanate (0.24 mL), 2.76 mmol) and acetonitrile (20 mL). The crude product was recrystallized from acetonitrile/chloroform. Yield: 121 mg (21%). |
Here is a chemical reaction formula: Reactants are m2:ClC1=CN=C2C(C(NC2=C1)=O)C(C1=CC(=CS1)Cl)=O, amount is: 0.0 ;m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ;m0_m1:ClC1=CN=C2C(C(NC2=C1)=O)C(C1=CC(=CS1)Cl)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CN=C2C(C(N(C2=C1)C(=O)N)=O)C(C1=CC(=CS1)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 6-chloro-3-(4-chloro-2-thenoyl)-4-azaoxindole according to the procedure of Example 2C using 6-chloro-3-(4-chloro-2-thenoyl)-4-azaoxindole (850 mg, 2.7 mmol), N-chlorosulfonyl isocyanate (0.35 mL, 4.0 mmol) and acetonitrile (30 mL). The crude product was recrystallized from acetic acid. Yield: 280 mg (29%). |
Here is a chemical reaction formula: Reactants are m0_m1:ClC=1N=C2C(C(NC2=CC1)=O)C(C1=CC=CS1)=O, amount is: 0.0 MOLE;m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ;m4:C(C)#N, amount is: 0.0 ;m2:ClC=1N=C2C(C(NC2=CC1)=O)C(C1=CC=CS1)=O, amount is: 0.0 ;m5:ClS(=O)(=O)NC=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6:CS(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1N=C2C(C(N(C2=CC1)C(=O)N)=O)C(C1=CC=CS1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 5-chloro-3-(2-thenoyl)-4-azaoxindole (Example 1B), according to the procedure of Example 2C, using 5-chloro-3-(2-thenoyl)-4-azaoxindole (500 mg, 1.79 mmol), N-chlorosulfonyl isocyanate (0.18 mL, 2.15 mmol), and acetonitrile (15 mL). The crude N-chlorosulfonyl carboxamide was hydrolyzed by stirring in DMSO (1.5 mL) for 1 hour in a flask open to the air. The product was precipitated by addition of water and the precipitate was collected by filtration, and recrystallized from acetic acid. Yield: 36 mg (6%). MS m/e (relative percent) 323 (7), 321 (17), 280 (9), 278 (24), 196 (22), 194 (62), 170 (25), 168 (100). Exact mass calc'd for C13H8ClN3O3 S: 320.9975; found: 320.9977. IR (KBr disc) 1724, 1623, 1570, 1512, 1415 cm-1. M.p. 222°-224° C. |
Here is a chemical reaction formula: Reactants are m4:ClS(=O)(=O)NC=O, amount is: 0.0 MOLE;m2:ClC=1N=C2C(C(NC2=CC1)=O)C(=O)C=1OC=CC1, amount is: 0.0 ;m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ;m0_m1:ClC=1N=C2C(C(NC2=CC1)=O)C(=O)C=1OC=CC1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1N=C2C(C(N(C2=CC1)C(=O)N)=O)C(=O)C=1OC=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 5-chloro-3-(2-furoyl)-4-azaoxindole (Example 23) according to the procedure of Example 2C, using 5-chloro-3-(2-furoyl)-4-azaoxindole (200 mg, 0.76 mmol), N-chlorosulfonyl isocyanate (0.10 mL, 1.1 mmol) and acetonitrile (8 mL). Hydrolysis of the N-chlorosulfonyl carboxamide was achieved by quenching the above reaction with water and allowing the mixture to stir at room temperature overnight. The product was collected by filtration and recrystallized from DMSO. Yield: 75 mg (32%). |
Here is a chemical reaction formula: Reactants are m4:C(C)#N, amount is: 0.0 ;m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ;m2:ClC=1N=C2C(C(NC2=CC1)=O)C(C1=CC(=CS1)Cl)=O, amount is: 0.0 ;m5:ClS(=O)(=O)NC=O, amount is: 0.0 MOLE;m0_m1:ClC=1N=C2C(C(NC2=CC1)=O)C(C1=CC(=CS1)Cl)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6:CS(=O)C, amount is: 0.0 ;m7:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1N=C2C(C(N(C2=CC1)C(=O)N)=O)C(C1=CC(=CS1)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 5-chloro-3-(4-chloro-2-thenoyl)-4-azaoxindole (Example 27) according to the procedure of Example 2C, using 5-chloro-3-(4-chloro-2-thenoyl)-4-azaoxindole (0.75 g, 2.39 mmol), N-chlorosulfonyl isocyanate (0.31 mL, 3.56 mmol), and acetonitrile (12 mL). Hydrolysis of the N-chlorosulfonyl carboxamide was achieved by stirring in DMSO (8 mL) for 4 hours at room temperature in a flask open to the air. The product was obtained by dilution of the mixture with water followed by filtration and recrystallized from acetic acid. Yield: 352 mg (41%). |
Here is a chemical reaction formula: Reactants are m4:C(C)#N, amount is: 0.0 ;m0_m1:ClC=1N=C2C(C(NC2=CC1)=O)C(C1=CC(=CS1)C)=O, amount is: 0.0 MOLE;m6:O, amount is: 0.0 MOLE;m5:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 MOLE;m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ;m2:ClC=1N=C2C(C(NC2=CC1)=O)C(C1=CC(=CS1)C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:CS(=O)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1N=C2C(C(N(C2=CC1)C(=O)N)=O)C(C1=CC(=CS1)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 5-chloro-3-(4-methyl-2-thenoyl)-4-azaoxindole (Example 30) according to the procedure of Example 2C, using 5-chloro-3-(4-methyl-2-thenoyl)-4-azaoxindole (0.90 g, 3.07 mmol), N-chlorosulfonyl isocyanate (0.40 mL, 4.60 mmol), and acetonitrile (15 mL). The crude N-chlorosulfonyl isocyanate was hydrolyzed by stirring in DMSO in a flask open to the air. The product was isolated by dilution with water and filtration, and was recrystallized from acetic acid. Yield: 190 mg (18%). M.P. 227°-228° C. |
Here is a chemical reaction formula: Reactants are m2:FC1=CN=C2C(C(NC2=C1)=O)C(C1=CC=CS1)=O, amount is: 0.0 ;m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ;m0_m1:FC1=CN=C2C(C(NC2=C1)=O)C(C1=CC=CS1)=O, amount is: 0.0 MOLE;m4:C(C)#N, amount is: 0.0 ;m5:ClS(=O)(=O)NC=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m7:O, amount is: 0.0 MOLE;m6:CS(=O)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC1=CN=C2C(C(N(C2=C1)C(=O)N)=O)C(C1=CC=CS1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 6-fluoro-3-(2-thenoyl)-4-azaoxindole (Example 5) according to the procedure of Example 2C, using 6-fluoro-3-(2-thenoyl)-4-azaoxindole (419 mg, 1.60 mmol), N-chlorosulfonyl isocyanate (0.2 mL, 2.3 mmol), and acetonitrile (8 mL). Reaction time: 3 days. The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO in a flask open to the air, diluting with water, and collecting the product by filtration. The product was recrystallized from acetic acid. Yield: 210 mg (43%). |
Here is a chemical reaction formula: Reactants are m4:C(C)#N, amount is: 0.0 ;m2:FC1=CN=C2C(C(NC2=C1)=O)C(C1=CC(=CS1)C)=O, amount is: 0.0 ;m5:ClS(=O)(=O)NC=O, amount is: 0.0 MOLE;m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ;m0_m1:FC1=CN=C2C(C(NC2=C1)=O)C(C1=CC(=CS1)C)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6:CS(=O)C, amount is: 0.0 ;m8_m7:C(C)(=O)O, amount is: 0.0 MOLE;m8_m7:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC1=CN=C2C(C(N(C2=C1)C(=O)N)=O)C(C1=CC(=CS1)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 6-fluoro-3-(4-methyl-2-thenoyl)-4-azaoxindole (Example 36) according to the procedure of Example 2C, using 6-fluoro-3-(4-methyl-2-thenoyl)-4-azaoxindole (614 mg, 2.22 mmol), N-chlorosulfonyl isocyanate (0.30 mL, 3.45 mmol) and acetonitrile (10 mL). The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO (4 mL) overnight in a flask open to the air. The product was isolated by dilution with water, filtration, and recrystallization from acetic acid. Yield: 249 mg (35%). M.p.>250°. |
Here is a chemical reaction formula: Reactants are m4:C(C)#N, amount is: 0.0 ;m0_m1:ClC=1C=C2C(C(NC2=CN1)=O)C(C1=CC=CS1)=O, amount is: 0.0 MOLE;m2:ClC=1C=C2C(C(NC2=CN1)=O)C(C1=CC=CS1)=O, amount is: 0.0 ;m5:ClS(=O)(=O)NC=O, amount is: 0.0 MOLE;m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CS(=O)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1C=C2C(C(N(C2=CN1)C(=O)N)=O)C(C1=CC=CS1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 5-chloro-3-(2-thenoyl)-6-azaoxindole (Example 3C) according to the procedure of Example 2C, using 5-chloro-3-(2-thenoyl)-6-azaoxindole (140 mg, 0.5 mmol), N-chlorosulfonyl isocyanate (65 L, 0.75 mmol), and acetonitrile (5 mL). The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO for 2 hours in a flask open to the air. The product was precipitated by addition of water and was collected by filtration. The solid was recrystallized from methanol. Yield: 27 mg (17%). |
Here is a chemical reaction formula: Reactants are m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ;m2:ClC=1N=C2C(C(NC2=CC1Cl)=O)C(C1=CC=CS1)=O, amount is: 0.0 ;m4:ClS(=O)(=O)NC=O, amount is: 0.0 MOLE;m0_m1:ClC=1N=C2C(C(NC2=CC1Cl)=O)C(C1=CC=CS1)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:CS(=O)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1N=C2C(C(N(C2=CC1Cl)C(=O)N)=O)C(C1=CC=CS1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 5,6-dichloro-3-(2-thenoyl)-4-azaoxindole (Example 6B) according to the procedure of Example 2C, using 5,6-dichloro-3-(2-thenoyl)-4-azaoxindole (194 mg, 0.62 mmol), N-chlorosulfonyl isocyanate (81 L, 0.93 mmol) acetonitrile (10 mL), and a temperature of 50° C. The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO in a flask open to the air. After dilution with water, the solid was collected by filtration and recrystallized from acetic acid. Yield: 129 mg (58%). |
Here is a chemical reaction formula: Reactants are m0_m1:C1(=CC=CS1)C(=O)C1C(NC2=CN=CC=C12)=O, amount is: 0.0 MOLE;m2:C1(=CC=CS1)C(=O)C1C(NC2=CN=CC=C12)=O, amount is: 0.0 ;m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CS1)C(=O)C1C(N(C2=CN=CC=C12)C(=O)N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 3-(2-thenoyl)-6-azaoxindole (Example 38) according to the procedure of Example 2C, using 3-(2-thenoyl)-6-azaoxindole (3.09 g, 12.6 mmol), N-chlorosulfonyl isocyanate (1.2 mL, 13.8 mmol) and acetonitrile (60 mL). Reaction time: 31/2 hours. |
Here is a chemical reaction formula: Reactants are m0_m1:C1(=CC=CC=C1)CC(=O)C1C(NC2=CN=CC=C12)=O, amount is: 0.0 MOLE;m4:C(C)#N, amount is: 0.0 ;m2:C1(=CC=CC=C1)CC(=O)C1C(NC2=CN=CC=C12)=O, amount is: 0.0 ;m5:ClS(=O)(=O)NC=O, amount is: 0.0 MOLE;m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CS(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)CC(=O)C1C(N(C2=CN=CC=C12)C(=O)N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 3-phenylacetyl-6-azaoxindole according to the procedure of Example 2C, using 3-phenylacetyl-6-azaoxindole (1.0 g, 3.9 mmol), N-chlorosulfonyl isocyanate (0.41 mL, 4.7 mmol) and acetonitrile (40 mL). Reaction time: 4 hours. The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO (6 mL) for 1 hour in a flask open to the air. After dilution with water, the product was collected by filtration, dried, and recrystallized from acetic acid. Yield: 172 mg (15%). M.p. 131°-133° C. (dec.). |
Here is a chemical reaction formula: Reactants are m2:C(C)(C)OC=1N=C2C(C(NC2=CC1)=O)C(C1=CC=CS1)=O, amount is: 0.0 ;m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ;m4:C(C)#N, amount is: 0.0 ;m5:ClS(=O)(=O)NC=O, amount is: 0.0 MOLE;m0_m1:C(C)(C)OC=1N=C2C(C(NC2=CC1)=O)C(C1=CC=CS1)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6:C(Cl)(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)(C)OC=1N=C2C(C(N(C2=CC1)C(=O)N)=O)C(C1=CC=CS1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 5-isopropoxy-3-(2-thenoyl)-4-azaoxindole (Example 9C) according to the procedure of Example 2C, using 5-isopropoxy-3-(2-thenoyl)-4-azaoxindole (70 mg, 0.23 mmol), N-chlorosulfonyl isocyanate (25 L, 0.29 mmol) and acetonitrile (1.5 mL). Reaction time: 4 hours. The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in chloroform for 3 days. After removal of the solvent in vacuo, the product was purified by flash chromatography on silica gel using 2:1 ethyl acetate/hexane as eluant and trituration with ether. Yield: 30 mg (37%). M.p. 194°-196° C. |
Here is a chemical reaction formula: Reactants are m2:C1(=CC=CS1)C(=O)C1C(NC2=CC=NC=C12)=O, amount is: 0.0 ;m3:C(=NS(=O)(=O)Cl)=O, amount is: 3.0 MILLIMOLE;m4:ClS(=O)(=O)NC=O, amount is: 0.0 MOLE;m0_m1:C1(=CC=CS1)C(=O)C1C(NC2=CC=CN=C12)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m8:C(C)#N, amount is: 0.0 ;m6:CO, amount is: 0.0 MOLE;m5:CS(=O)C, amount is: 0.0 ;m7:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C1(=CC=CS1)C(=O)C1C(N(C2=CC=NC=C12)C(=O)N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 3-(2-thenoyl)-4-azaoxindole (Example 4C) according to the procedure of Example 2C, using 3-(2-thenoyl)-5-azaoxindole (500 mg, 2.0 mmol), N-chlorosulfonyl isocyanate (0.26, 3.0 mmol), and acetonitrile (15 mL). Reaction time: 2.25 hours. The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO (1.5 mL) for 1.5 hours in a flask open to the air. Ether was added to give a two phase mixture followed by methanol, which gave a homogenous solution. On standing for a brief period, a green precipitate formed which was removed by filtration. The filtrate was allowed to stand overnight, during which time the product crystallized from the solution. This was collected by filtration. Yield: 39 mg (7%). M.p. 250°. |
Here is a chemical reaction formula: Reactants are m0_m1:C(C1=CC=CC=C1)(=O)C1C(NC2=CC=C(N=C12)Cl)=O, amount is: 0.0 MOLE;m2:C(C1=CC=CC=C1)(=O)C1C(NC2=CC=C(N=C12)Cl)=O, amount is: 0.0 ;m4:C(C)#N, amount is: 0.0 ;m5:ClS(=O)(=O)NC=O, amount is: 0.0 MOLE;m3:C(=NS(=O)(=O)Cl)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CS(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)(=O)C1C(N(C2=CC=C(N=C12)Cl)C(=O)N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 3-benzoyl-5-chloro-4-azaoxindole (Example 32) according to the procedure of Example 25, using 3-benzoyl-5-chloro-4-azaoxindole (2.73 g, 10.0 mmol), N-chlorosulfonyl isocyanate (1.3 mL, 15 mmol) and acetonitrile (80 mL). The reaction time was 20 hours. The crude N-chlorosulfonyl carboxamide was hydrolyzed by stirring in DMSO (15 mL) for 20 hours. The crude product was recrystallized from acetic acid and washed with methanol. Yield: 0.36 g (11%). |
Here is a chemical reaction formula: Reactants are m1_m4_m5:N1C=CC2=CC=CN=C12, amount is: 0.0 ;m3:C(C)I, amount is: 0.0 ;m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m5:CC(=O)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)N1C=CC2=CC=CN=C12, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 10 grams (0.0846 moles) of 7-azaindole (Aldrich (trademark)) were dissolved in 200 mL of reagent grade acetone at room temperature and treated with 10 grams (0.178 moles) of powdered KOH. After~2-3 minutes, 67 mL (0.846 moles) of ethyl iodide was added over a period of 5-10 minutes and the reaction mixture was stirred at room temperature for 30-40 minutes. Thin layer chromatography (TLC) using 95% methylene chloride/5% ethyl acetate showed complete consumption of the starting material and formation of a single less polar product. The reaction mixture was concentrated in vacuo and the residue was partitioned between water and methylene chloride (350 mL). The organic layer was separated and washed with water and brine and dried (sodium sulfate). Concentration of the organic extract in vacuo gave a yellow-brown oil which was purified on a silica gel column eluting with methylene chloride/ethyl acetate (95%/5%). A total of 11.15 grams (90%) of pure final product (light yellow oil) was obtained. |
Here is a chemical reaction formula: Reactants are m2:ClC=1C=C2CC(N(C2=NC1)CC)=O, amount is: 0.0 ;m0_m1:ClC=1C=C2CC(N(C2=NC1)CC)=O, amount is: 0.0 MOLE;m3:O1C(=CC=C1)C(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:CN(C)C=O, amount is: 0.0 ,Catalysts are m4:CN(C1=CC=NC=C1)C, amount is: 0.0 .Products are 0:ClC=1C=C2C(C(N(C2=NC1)CC)=O)C(=O)C=1OC=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 5-chloro-1-ethyl-7-azaoxindole (Example 53D) according to the procedure of Example 53E, using 5-chloro-1-ethyl-7-azaoxindole (405 mg, 2.06 mmol), 4-dimethylaminopyridine (500 mg, 4.09 mmol), 2-furoyl chloride (0.22 mL, 2.23 mmol) and DMF (10 mL). The solid product obtained following chromatography was recrystallized from hexane. The yield was 110 mg (18%). |
Here is a chemical reaction formula: Reactants are m2_m4_m3:C(#N)C1=CC=C(C=O)C=C1, amount is: 0.0 ;m2_m4_m3:Cl.NO, amount is: 0.0 ;m1:C(#N)C1=CC=C(C=O)C=C1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m4_m3:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C1=CC=C(C=NO)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: This material was prepared from 4-cyanobenzaldehyde according to Kawase and Kikugawa (J. Chem. Soc., Perkin Trans I 1979, 643). To a solution of 4-cyanobenzaldehyde (1.31 g, 10 mmol) in 1:1EtOH:pyridine (10 mL) was added hydroxylamine hydrochloride (0.70 g, 10 mmol). The resulting solution was stirred at room temperature for 18 h and was concentrated in vacuo to one-half volume. To this solution was added ice water, causing the product to crystallize from solution. Recrystallization from EtOH--water followed by drying over P2O5 afforded 1.46 g (100%) of the desired oxime; mp: 167.8-169.4° C. |
Here is a chemical reaction formula: Reactants are m3:Cl[O-].[Na+], amount is: 0.0 ;m1_m4_m2:C(#N)C1=CC=C(C=NO)C=C1, amount is: 0.0 ;m1_m4_m2:C(=C)CC(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C1=CC=C(C=C1)C1=NOC(C1)CC(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-cyanobenzaldoxime (see Ex 2) (312 g, 2.13 mol) in tetrahydrofuran (3 L) at room temperature was added vinylacetic acid (552 g, 6.41 mol). The yellow solution was cooled in an ice bath and sodium hypochlorite solution (5200 mL)was added in a dropwise fashion over 2 h. After stirring overnight at room temperature the reaction was quenched with a 5% citric acid solution and diluted with 200 mL ether. The layers were separated and the aqueous acidified to pH 4 using citric acid. The acid layer was washed twice with 200 mL ether, the ether layers combined and extracted with saturated sodium bicarbonate solution. After acidifying the basic layer with citric acid, the product was extracted into 400 mL ether. The organic phase was washed three times with 150 mL water, once with brine, dried (MgSO4) and concentrated to give 220 g of 3-(4-cyanophenyl)isoxazolin-5-ylacetic acid as a white solid. Recrystallization from 25% water/ethanol yielded 165 g of analytically pure material; 1H NMR (300 MHz, CDCl3) δ 7.77-7.76 (d, J=1.8 Hz, 2H), 7.72-7.71 (d, J=1.8 Hz, 2H), 5.22-5.14 (m, 1H), 3.63-3.54 (dd, J=10.6 Hz, 16.8 Hz, 1H), 3.19-3.11 (dd, J=7.3 Hz, 16.8 Hz, 1H), 3.00-2.93 (dd, J=6.2 Hz, 16.5 Hz, 1H), 2.79-2.72 (dd, J=7.3 Hz, 16.5 Hz, 1H); IR (KBr): 3202, 2244, 1736, 1610, 1432, 1416, 1194, 1152, 928, 840, 562 cm-1. Anal. Calcd for C12H10N2O3 : C, 62.61; H, 4.38; N, 12.17. Found: C, 62.37; H, 4.47; N, 11.71. |
Here is a chemical reaction formula: Reactants are m3:[Cl-].[Zn+2].[Cl-], amount is: 0.0 ;m0_m1_m4_m2:CN(S(=O)(=O)N1C=NC=C1)C, amount is: 0.0 ;m0_m1_m4_m2:[Li]C(C)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m0_m1_m4_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Cl-].CN(S(=O)(=O)N1C(=NC=C1)[Zn+])C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-dimethylsulfamoyl-imidaz-2-yl zinc chloride was prepared in situ by lithiation of N-dimethylsulfamoylimidazole (0.97 g, 5.5 mmol) in THF (20 mL) with t-BuLi (1.7M, 6.7 mL), followed by quenching with zinc chloride (1.87 g, 13.75 mmol). |
Here is a chemical reaction formula: Reactants are m2_m1_m3:C(CCCCCCC)[Mg]Br, amount is: 0.0 ;m2_m1_m3:C1CCOC1, amount is: 0.0 ;m2_m1_m3:C1CCOC1, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(CCCCCCC)C(=O)CCCCCCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4.0 g (14.5 mmol) of the LIVb in 100 mL of THF was added 20 mL (40 mmol) of 2M octylmagnesium bromide in THF dropwise. After stirring 3.5 h, the solution was quenched with saturated NH4Cl, acidified with 1N HCl, and was extracted with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel. Elution with 7.5% ethyl acetate in hexanes gave 4.86 g (88%) of the bis-octyl ketone LIVc as an oil. 1H NMR (300 MHz, CDCl3) δ 4.55 (s, 2H, CH), 2.64 (dt, 4H, CH2), 1.62 (m, 4H, CH2), 1.42 (s, 6H, CH3), 1.27 (broad s, 20H, CH2), 0.88 (t, 6H, CH3); MS (CI,NH3) m/e 383 (M+1). |
Here is a chemical reaction formula: Reactants are m3_m6_m4:BrC=1C=NC=C(C1)Br, amount is: 0.0 ;m3_m6_m4:C(C1=CC=CC=C1)O, amount is: 0.0 ;m1_m2:[Na], amount is: 0.0 ;m1_m2:C(C1=CC=CC=C1)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 ,Catalysts are m3_m6_m4:[Cu], amount is: 0.0 .Products are 0:BrC=1C=NC=C(C1)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Under a nitrogen atmosphere, small pieces of sodium (1.48 g, 64.4 mmol) were added to benzyl alcohol (17.11 g, 158.0 mmol), and the mixture was stirred and heated at 70° C. for 18 h. To the stirring, viscous mixture was added 3,5-dibromopyridine (5.00 g, 21.1 mmol), copper powder (255 mg, 4.0 mmol), and benzyl alcohol (15 mL). The mixture was further heated at 100° C. for 48 h. The reaction mixture was allowed to cool to ambient temperature, diluted with water (50 mL), and extracted with diethyl ether (5×50 mL). The combined ether extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation. Vacuum distillation removed excess benzyl alcohol, bp 68°-72° C. at 2.6 mm Hg. Further vacuum distillation afforded 3.17 g (38.0%) of 3-bromo-5-benzyloxypyridine as a white, crystalline solid, mp 64°-66° C. |
Here is a chemical reaction formula: Reactants are m4:[OH-].[Na+], amount is: 0.0 MOLE;m1_m2_m3:BrC=1C=NC=C(C1)Br, amount is: 0.0 ;m1_m2_m3:CN(C=O)C, amount is: 0.0 ;m1_m2_m3:[O-]C1=CC=CC=C1.[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C=NC=C(C1)OC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium phenoxide trihydrate (7.50 g, 44.1 mmol) was dried under vacuum at 65° C. for 18 h at 0.6 mm Hg to yield 5.08 g of sodium phenoxide. Under a nitrogen atmosphere, 3,5-dibromopyridine (4.00 g, 16.9 mmol) and anhydrous N,N-dimethylformamide (40 mL) were added to the sodium phenoxide (5.08 g, 43.8 mmol). The resulting mixture was stirred at 110° C. for 44 h. After cooling to ambient temperature, water (75 mL) was added, and the pH was adjusted to 13.0 using 30% NaOH solution. The solution was extracted with diethyl ether (4×60 mL). The combined ether extracts were washed with saturated NaCl solution (50 mL), dried (NaSO4), filtered and concentrated by rotary evaporation to a brown oil (4.0 g). The oil was vacuum distilled, collecting a forerun (317 mg), bp 48°-65° C. at 0.05 mm Hg. Further distillation afforded 3.35 g (79.8%) of 3-bromo-5-phenoxypyridine as a pale-yellow oil, bp 75-112° C. at 0.05 mm Hg (lit. bp 110°-115° C. at 1.7 mm Hg, see K. Fujikawa, et al. Agr. Biol. Chem. 34:68 (1970). |
Here is a chemical reaction formula: Reactants are m3_m1:[K], amount is: 0.0 ;m3_m1:CC(C)O, amount is: 0.0 ;m2_m4:BrC=1C=NC=C(C1)Br, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m2_m4:[Cu], amount is: 0.0 .Products are 0:BrC=1C=NC=C(C1)OC(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Under a nitrogen atmosphere, 2-propanol (30 mL) was added to potassium (2.4 g, 61.4 mmol) at 0° C., and the mixture was stirred at 0° C. for 30 min. To the resulting solution was added 3,5-dibromopyridine (4.74 g, 20.0 mmol) and copper powder (250 mg, 3.9 mmol). The mixture was heated under reflux under a nitrogen atmosphere for 70 h. Upon cooling to ambient temperature, the mixture was concentrated under high vacuum to a solid, which was diluted with water (200 mL) and extracted with diethyl ether (3×150 mL). The combined ether extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation to a dark-brown oil (3.71 g). Purification by column chromatography on silica gel, eluting with 10→20% (v/v) diethyl ether in benzene afforded 1.38 g (31.9%) of 3-bromo-5-isopropoxypyridine as a volatile, colorless oil. |
Here is a chemical reaction formula: Reactants are m1_m2:BrC=1C=NC=C(C(=O)O)C1, amount is: 0.0 ;m1_m2:S(=O)(Cl)Cl, amount is: 0.0 ;m5_m3:[BH4-].[Na+], amount is: 0.0 ;m4:[NH4+].[Cl-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m3:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C=NC=C(C1)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Under a nitrogen atmosphere, a solution of 5-bromonicotinic acid (5.05 g, 25.0 mmol) and thionyl chloride (10 mL) was stirred and heated. The excess thionyl chloride was removed by distillation, and the residue was dried briefly under high vacuum. To the resulting light-yellow solid in dry tetrahydrofuran (40 mL) was added sodium borohydride (1.90 g, 50.0 mmol) at 0° C. under a nitrogen atmosphere. The mixture was stirred 1 h at 0° C. and allowed to warm to ambient temperature. The mixture was added to a cold, saturated aqueous NH4Cl solution (100 mL) and extracted with diethyl ether (3×50 mL). The combined ether extracts were dried (Na2 SO4), filtered, and concentrated by rotary evaporation to a semisolid (2.77 g). Thin layer chromatography analysis on silica gel indicated mostly 5-bromonicotinic acid; therefore the semisolid was partitioned between ether and saturated aqueous NaHCO3 solution. The ether layer was separated and concentrated by rotary evaporation to a residue (0.75 g). Purification by column chromatography on silica gel, eluting with ethyl acetate-hexane (1:1, v/v) afforded 379 mg (8.1%) of 3-bromo-5-hydroxymethylpyridine. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m3:CI, amount is: 0.0 ;m1_m5_m2:BrC=1C=NC=C(C1)CO, amount is: 0.0 ;m1_m5_m2:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C=NC=C(C1)COC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Under a nitrogen atmosphere, a solution of 3-bromo-5-hydroxymethylpyridine (379 mg, 2.0 mmol) in dry tetrahydrofuran (10 mL) was treated at ambient temperature with sodium hydride (160 mg, 4.0 mmol, 60% dispersion in mineral oil). After stirring 5 min at ambient temperature, the opaque, yellow mixture was treated with methyl iodide (342 mg, 2.4 mmol). After stirring 2 h at ambient temperature, the mixture was added to cold water (30 mL) and extracted with diethyl ether (3×20 mL). The combined ether extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation to an orange oil (429 mg). Purification by column chromatography on silica gel, eluting with 15% (v/v) ethyl acetate in hexane afforded 266 mg (65.3%) of 3-bromo-5-methoxymethylpyridine as a colorless oil. |
Here is a chemical reaction formula: Reactants are m1_m2:C(=O)(O)CCC1=CC=C(C=C1)SCC=1N=C(N(C1C(=O)OCC)CC1=CC2=C(OCO2)C=C1Cl)CCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)CCC1=CC=C(C=C1)SCC=1N=C(N(C1C(=O)O)CC1=CC2=C(OCO2)C=C1Cl)CCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 540 mg of the ester obtained in Example 63 is dissolved in 20 ml of ethanol and 10 ml of 2N soda and the solution is agitated for 5 hours at ambient temperature. The solvent is evaporated off under reduced pressure, the aqueous phase is filtered off, it is acidified using acetic acid, the precipitate is separated off, washed with water, dried at 50° C. under reduced pressure. The residue is taken up in isopropyl ether, dried and 420 mg of expected product is obtained. M.p.=171° C. |
Here is a chemical reaction formula: Reactants are m3_m7:C(C1=CC=CC=C1)Br, amount is: 0.0 ;m1:[H-].[Na+], amount is: 0.0 ;m2_m6:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m4:[Cl-].[NH4+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m7:CN(C=O)C, amount is: 0.0 ;m2_m6:CN(C=O)C, amount is: 0.0 ;m5:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1C=CC=2C(=CC=CC12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium hydride (95%; 0.37 g) was suspended in 10 ml of dimethylformamide and cooled to a temperature ranging from 0° to 5° C. with stirring, under an argon gas atmosphere. To the resulting mixed liquid, there was dropwise added a solution of 2.00 g of indole-4-carbaldehyde in 5 ml of dimethylformamide over 15 minutes. After completion of the dropwise addition, the mixture was stirred at a temperature ranging from 0° to 5° C. for 30 minutes. To the reaction solution, there was added a solution of 2.47 g of benzyl bromide in 5 ml of dimethylformamide, followed by stirring at room temperature for 2 hours. The reaction solution was poured into 200 ml of a 10% ammonium chloride aqueous solution, followed by extraction with ethyl acetate (200 ml×2). After washing the extract with a saturated common salt solution, it was dried over anhydrous sodium sulfate, followed by evaporation of the solvent under reduced pressure to give 3.18 g of 1-benzylindole-4-carbaldehyde as brown crystals. The yield thereof was found to be 98%. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)O, amount is: 0.0 ;m1_m2_m3:C(C1=CC=CC=C1)N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m1_m2_m3:N1CCCCC1, amount is: 0.0 ;m4:S1C(NC(C1)=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1C=CC2=C(C=CC=C12)C=C1C(NC(S1)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 60 ml of ethanol, there were dissolved 3.00 g of 1-benzylindole-4-carbaldehyde prepared in Example 1 and 0.22 g of piperidine, followed by addition of 2.99 g of 2,4-thiazolidinedione to the resulting solution and heating the mixture under reflux for 24 hours. To the reaction solution, there was added 120 ml of diethyl ether and the mixture was stirred at 0° C. for one hour. The crystals precipitated were filtered off and washed with a diethyl ether/ethanol (2:1) mixed solvent. The crystals were dried under reduced pressure to give 3.24 g of 5-(1-benzylindol-4-yl)methylene-2,4-thiazolidinedione as yellow crystals. The yield thereof was found to be 76%. |
Here is a chemical reaction formula: Reactants are m5_m9:C(C1=CC=CC=C1)N1C=CC2=C(C=CC=C12)C=C1C(NC(S1)=O)=O, amount is: 0.0 ;m3:II, amount is: 0.0 MOLE;m8:[Cl-].[NH4+], amount is: 0.0 MOLE;m4:II, amount is: 0.0 MOLE;m2:[Mg], amount is: 0.0 MOLE;m1_m10:[Mg], amount is: 0.0 MOLE;m7:[Mg], amount is: 0.0 MOLE;m6:[Mg], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m9:CO, amount is: 0.0 ;m1_m10:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1C=CC2=C(C=CC=C12)CC1C(NC(S1)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To metal magnesium, there was added methanol in an amount sufficient for immersing the magnesium metal and then a small amount of iodine powder was added thereto, under an argon gas atmosphere. The mixture was allowed to stand till foaming was initiated and then stirred till the color of the iodine disappeared. To the mixed liquid, there were added 3.00 g of 5-(1-benzylindol-4-yl)methylene-2,4-thiazolidinedione prepared in Example 2 and 210 ml of methanol, followed by stirring at room temperature and addition of 4.36 g of magnesium powder over 2 hours. After the addition of the magnesium powder, the resulting mixture was stirred at room temperature for 2 hours. The reaction solution was poured into 2 l of a 20% ammonium chloride aqueous solution, followed by extraction with dichloromethane (1 l×3). The resulting extract was washed with a 10% citric acid aqueous solution and a saturated common salt solution in this order, followed by drying the extract over anhydrous sodium sulfate and evaporation of the solvent under reduced pressure to give 2.24 g of 5-(1-benzylindol-4-yl)methyl-2,4-thiazolidinedione as yellow crystals. The yield thereof was found to be 74%. |
Here is a chemical reaction formula: Reactants are m3_m4_m5:O1CCCC1, amount is: 0.0 ;m3_m4_m5:O, amount is: 0.0 ;m1_m2:COC(=O)C1=CC=C(CN2C=CC3=C(C=CC=C23)CC2C(NC(S2)=O)=O)C=C1, amount is: 0.0 ;m1_m2:O.[OH-].[Li+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m4_m5:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)=C1CC=C(CN2C=CC3=C(C=CC=C23)CC2C(NC(S2)=O)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 2.00 g of 5-[1-(4-methoxycarbonylbenzyl)indol-4-yl]methyl-2,4-thiazolidinedione prepared in Example 9 and 0.43 g of lithium hydroxide monohydrate, there were, in order, added 40 ml of tetrahydrofuran, 40 ml of water and 20 ml of methanol and the resulting mixture was stirred at 60° C. for 2 hours. After concentrating the reaction solution to about 40 ml, the concentrate was neutralized with a 10% citric acid aqueous solution, followed by extraction with dichloromethane (100 ml×3). The extract was washed with a saturated common salt solution, dried over anhydrous sodium sulfate, followed by evaporation of the solvent under reduced pressure to give 1.54 g of 5-[1-(4-carbonylbenzyl)indol-4-yl]methyl-2,4-thiazolidinedione as pale yellow crystals. The yield thereof was found to be 80%. |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)(=O)Cl, amount is: 0.0 ;m1:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)(=O)N1C=CC=2C(=CC=CC12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 11 were repeated except for using 725 mg of indole-4-carbaldehyde and 773 mg of benzoyl chloride instead of phenylacetyl chloride to give 260 mg of 1-benzoylindole-4-carbaldehyde as colorless crystals. The yield thereof was found to be 21%. |
Here is a chemical reaction formula: Reactants are m2:CC1=C(N=C(O1)C1=CC=CC=C1)CN1C=CC=2C(=CC=CC12)C(=O)OC, amount is: 0.0 ;m1_m6:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 0.0 ;m3_m4_m5:O, amount is: 0.0 ;m3_m4_m5:[OH-].[Na+], amount is: 0.0 MOLE;m3_m4_m5:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:O1CCCC1, amount is: 0.0 ;m1_m6:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OCC1=C2C=CN(C2=CC=C1)CC=1N=C(OC1C)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 114 mg of lithium aluminum hydride in 5 ml of tetrahydrofuran, there was dropwise added a solution obtained by dissolving, in 5 ml of tetrahydrofuran, 1.04 g of methyl 1-[(5-methyl-2-phenyloxazol-4-yl)methyl]indole-4-carboxylate prepared in Example 28 over 30 minutes, with ice-cooling and under an argon gas atmosphere. After stirring the reaction solution for one hour, there were, in order, added 0.11 ml of water, 0.11 ml of a 15% aqueous sodium hydroxide solution and 0.33 ml of water to the reaction solution, followed by stirring the mixture for 2 hours. The insolubles were filtered off, the resulting filtrate was concentrated and the residue was dried under reduced pressure to give 949 mg of 4-hydroxymethyl-1-[(5-methyl-2-phenyloxazol-4-yl)methyl]indole as colorless crystals. The yield thereof was found to be 99%. |
Here is a chemical reaction formula: Reactants are m2_m6:N1C=CC=2C(=CC=CC12)C(=O)OC, amount is: 0.0 ;m4:[Cl-].[NH4+], amount is: 0.0 MOLE;m3_m7:C(C)C1=CC=C(C(=O)Cl)C=C1, amount is: 0.0 ;m1:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:CN(C=O)C, amount is: 0.0 ;m2_m6:CN(C=O)C, amount is: 0.0 ;m3_m7:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)C1=CC=C(C(=O)N2C=CC=3C(=CC=CC23)C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium hydride (95%; 0.30 g) was suspended in 10 ml of dimethylformamide and the suspension was stirred while cooling the same at a temperature ranging from 0° to 5° C. To this mixed liquid, there was dropwise added a solution of 2.00 g of methyl indole-4-carboxylate in 5 ml of dimethylformamide over 15 minutes. After the completion of the dropwise addition, the reaction solution was stirred at a temperature ranging from 0° to 5° C. for 30 minutes. To the reaction solution, there was added a solution of 2.09 g of 4-ethylbenzoyl chloride in 5 ml of dimethylformamide, followed by stirring at room temperature for 2 hours. The reaction solution was poured into 200 ml of a 10% ammonium chloride aqueous solution, followed by extraction with ethyl acetate (200 ml×2). The extract was washed with a saturated common salt solution, dried over anhydrous sodium sulfate and the solvent was removed through distillation under reduced pressure to thus give 3.51 g of a residue. The residue was purified by silica gel chromatography (hexane:ethyl acetate=11:1) to give 2.18 g of methyl 1-(4-ethylbenzoyl)indole-4-carboxylate as colorless crystals. The yield thereof was found to be 62%. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)C1=CC=C(CN2C=CC3=C(C=CC=C23)CO)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:ClCCl, amount is: 0.0 ,Catalysts are m1_m2:[O-2].[O-2].[Mn+4], amount is: 0.0 .Products are 0:C(C)C1=CC=C(CN2C=CC=3C(=CC=CC23)C=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 1.00 g of 1-(4-ethylbenzyl)-4-(hydroxymethyl) indole prepared in Example 34 and 2.31 g of activated manganese dioxide (~85%), there was added 30 ml of dichloromethane and the resulting mixture was stirred at room temperature for 4 hours. The reaction solution was filtered, followed by washing with dichloromethane (50 ml×2). The solvent was distilled off, under reduced pressure, from the resulting filtrate to give 0.92 g of 1-(4-ethylbenzyl)indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 93%. |
Here is a chemical reaction formula: Reactants are m3_m8:C(C=C)(=O)OC, amount is: 0.0 ;m2_m7:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m1:[H-].[Na+], amount is: 0.0 ;m4:[Cl-].[NH4+], amount is: 0.0 MOLE;m5:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m8:CN(C=O)C, amount is: 0.0 ;m2_m7:CN(C=O)C, amount is: 0.0 ;m6:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(=O)CCN1C=CC=2C(=CC=CC12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium hydride (95%; 383 mg) was suspended in 10 ml of dimethylformamide under an argon gas atmosphere. To the suspension, there was dropwise added a solution of 2.00 g of indole-4-carbaldehyde in 10 ml of dimethylformamide with ice-cooling and stirring. After stirring the reaction mixture at room temperature for 25 minutes, it was again ice-cooled followed by dropwise addition of a solution of 1.33 g of methyl acrylate in 10 ml of dimethylformamide and stirring at room temperature for 19 hours. The reaction system was poured into 400 ml of a 10% ammonium chloride solution, followed by addition of a 2% HCl aqueous solution till the system became acidic and extraction with ethyl acetate (200 ml×2). After drying the extract over anhydrous magnesium sulfate, the solvent was removed by distillation under reduced pressure and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to thus give 3.68 g of a pale yellow oily substance. This was dissolved in 40 ml of dimethylformamide, followed by addition of 2.70 g of methyl iodide and 2. 58 g of potassium carbonate and stirring the mixture at room temperature for 1.5 hour. The mixture was poured into 400 ml of a 10% ammonium chloride aqueous solution and extracted with ethyl acetate (200 ml×2). After drying the resulting extract over anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure and the resulting crude product was purified by silica gel column chromatography to give 848 mg of 1-(2-methoxycarbonylethyl)indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 27%. |
Here is a chemical reaction formula: Reactants are m1_m5:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m3:C1(=CC(=CC=C1)N=C=O)C, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 ;m4:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:CN(C=O)C, amount is: 0.0 ;m6:CCCCCC.C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C1(=CC(=CC=C1)NC(=O)N1C=CC=2C(=CC=CC12)C=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Indole-4-carbaldehyde (435 mg) was dissolved in 8 ml of dimethylformamide at room temperature under an argon gas atmosphere, then 126 mg of sodium hydride (content 60%) was added to the resulting solution and the mixture was stirred for 30 minutes, then 439 mg of m-tolylisocyanate was added thereto and the resulting mixture was stirred for one hour. The reaction solution was added to 50 ml of water followed by extraction with ethyl acetate (50 ml×2). The resulting organic phase was washed with water (50 ml×2), dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure to give a crude product. This was subjected to silica gel chromatography (eluent: hexane/ethyl acetate=4/1) to give 736 mg of 1-(m-tolylcarbamoyl)indole-4-carbaldehyde as pale yellow crystals. The yield thereof was found to be 88%. |
Here is a chemical reaction formula: Reactants are m1:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m2:FC1=C(CBr)C=CC=C1, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC1=C(CN2C=CC=3C(=CC=CC23)C=O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 725 mg of indole-4-carbaldehyde and 2-fluorobenzyl bromide instead of the benzyl bromide used in Example 1 to give 1.22 g of 1-(2-fluorobenzyl)indole-4-carbaldehyde as yellow crystals. The yield thereof was found to be 96%. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m1_m2_m3:FC1=CC=C(CBr)C=C1, amount is: 0.0 ;m1_m2_m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m4_m5:N1CCCCC1, amount is: 0.0 ;m4_m5:S1C(NC(C1)=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:C(C)#N, amount is: 0.0 ;m8:C(C)OCC, amount is: 0.0 ;m7:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC=C(CN2C=CC3=C(C=CC=C23)C=C2C(NC(S2)=O)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: There were dissolved, in 20 ml of acetonitrile, 2.00 g of indole-4-carbaldehyde and 5.20 g of 4-fluorobenzyl bromide, followed by addition of 9.52 g of potassium carbonate and stirring for 16 hours while heating the reaction mixture to 52° C. The reaction solution was cooled down to room temperature, followed by removal of potassium carbonate through filtration and removal of the solvent through evaporation under reduced pressure. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to give a yellow oily substance. The substance was dissolved in 40 ml of ethanol, followed by addition, to the solution, of 240 mg of piperidine and 3.4 g of 2,4-thiazolidinedione and reflux of the mixture with heating over 22 hours. The reaction mixture was cooled in an ice bath followed by addition of 80 ml of diethyl ether, stirring at that temperature for one hour, then separation of the precipitated yellow crystals through filtration and washing with diethyl ether to give 3.95 g of 5-[1-(4-fluorobenzyl)indol-4-yl]methylene-2,4-thiazolidinedione as yellow crystals. The yield thereof was found to be 81%. |
Here is a chemical reaction formula: Reactants are m2:FC1=C(CBr)C=CC=C1F, amount is: 0.0 ;m1:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC1=C(CN2C=CC=3C(=CC=CC23)C=O)C=CC=C1F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 580 mg of indole-4-carbaldehyde and 911 mg of 2,3-difluorobenzyl bromide in place of the benzyl bromide used in Example 1 to give 841 mg of 1-(2,3-difluorobenzyl)indole-4-carbaldehyde as pale brown crystals. The yield thereof was found to be 76%. |
Here is a chemical reaction formula: Reactants are m2:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m1:FC1=C(CCl)C(=CC=C1)F, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC1=C(CN2C=CC=3C(=CC=CC23)C=O)C(=CC=C1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 2.35 g of 2,6-difluorobenzyl chloride and 2.00 g of indole-4-carbaldehyde as a starting material to give 3.74 g of 1-(2,6-difluorobenzyl)indole-4-carbaldehyde as pale yellow crystals. The yield thereof was found to be 100%. |
Here is a chemical reaction formula: Reactants are m1:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m2:FC=1C=C(CBr)C=CC1F, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC=1C=C(CN2C=CC=3C(=CC=CC23)C=O)C=CC1F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 725 mg of indole-4-carbaldehyde and 1.14 g of 3,4-difluorobenzyl bromide in place of the benzyl bromide used in Example 1 to give 1.32 g of 1-(3,4-difluorobenzyl)indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 97%. |
Here is a chemical reaction formula: Reactants are m1:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m2:CS(=O)(=O)OCC1=C(C=CC=C1)C(F)(F)F, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC(C1=C(CN2C=CC=3C(=CC=CC23)C=O)C=CC=C1)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 725 mg of indole-4-carbaldehyde and 2-trifluoromethylbenzyl methanesulfonate in place of the benzyl bromide used in Example 1 to give 1.44 g of 1-(2 -trifluoromethylbenzyl)indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 95%. |
Here is a chemical reaction formula: Reactants are m2:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m1:CS(=O)(=O)OCC1=CC(=CC=C1)C(F)(F)F, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC(C=1C=C(CN2C=CC=3C(=CC=CC23)C=O)C=CC1)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 3.68 g of 3-trifluoromethylbenzyl methanesulfonate and 2.00 g of indole-4-carbaldehyde to give 4.12 g of 1-(3-trifluoromethylbenzyl) indole-4-carbaldehyde as yellow crystals. The yield thereof was found to be 99%. |