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Here is a chemical reaction formula: Reactants are m6_m3:C(=O)[O-].[NH4+], amount is: 0.0 ;m1_m4_m2_m5:[N+](=O)([O-])C(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CCCCC, amount is: 0.0 ;m1_m4_m2_m5:C(=O)[O-].[NH4+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m5:CO, amount is: 0.0 ,Catalysts are m6_m3:[Pd], amount is: 0.0 ;m1_m4_m2_m5:[Pd], amount is: 0.0 .Products are 0:NC(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CCCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of tetraethyl 3-nitrooctane-1,1-bisphosphonate (0.70 g, 1.62 mmol) in methanol (4 mL) was added ammonium formate (0.45 g, 6.9 mmol) and 10% palladium on carbon (0.070 g). After 24 hours, more 10% palladium on carbon (0.035 g) and ammonium formate (0.45 g, 6.9 mmol) were added. After stirring for a total of 4 days, the reaction mixture was filtered, rinsing the residue with methanol, and concentrated. The residue was taken up in brine (5 mL) and extracted with dichloromethane (4×15 mL), dried (Na2SO4) and concentrated to give the title compound (0.60 g, 95%) as an oil. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:NC(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CCCCC, amount is: 0.0 ;m1_m3_m2:Br[Si](C)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[NH4+].[NH4+].[NH4+].NC(CC(P([O-])(=O)[O-])P(O)(=O)[O-])CCCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of tetraethyl 3-aminooctane-1,1-bisphosphonate (0.45 g, 1.12 mmol) in dry dichloromethane (1.1 mL) was added bromotrimethylsilane (1.05 mL, 7.85 mmol) via syringe. After 18 hours, the mixture was concentrated under vacuum. To the residue was added 3N NH4OH (8 mL) which was stirred for 30 minutes at room temperature. The solvent was removed in vacuo and the residue concentrated from methanol (2 mL) to give 0.40 g of 3-aminooctane-1,1-bisphosphonic acid, triammonium salt as a white powder. |
Here is a chemical reaction formula: Reactants are m3_m4:COC=1C=C(C=CC1)C=1OC2=C(C1C)C=CC=C2, amount is: 0.0 ;m3_m4:Cl.N1=CC=CC=C1, amount is: 0.0 MOLE;m2:COC=1C=C(C=CC1)C=1OC2=C(C1C)C=CC=C2, amount is: 0.0 MOLE;m5:COC, amount is: 0.0 MOLE;m6:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m7:O1CCOCC1, amount is: 0.0 MOLE,Catalysts are m8:[Ti](Cl)(Cl)(Cl)Cl.[Zn], amount is: 0.0 MOLE.Products are 0:OC(COC=1C=C(C=CC1)C=1OC2=C(C1C)C=CC=C2)CO;0:OC=1C=C(C=CC1)C=1OC2=C(C1C)C=CC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The ester which results from the condensation of 2'-hydroxyacetophenone and m-anisic acid is converted to 2-(3-methoxyphenyl)-3-methylbenzofuran by reductive cyclization in dioxane with a titanium tetrachloride/zinc metal catalyst according to the method of Banerji and Nayak, J. Chem. Soc., Chem. Comm., (1990), 150. The 2-(3-methoxyphenyl)-3-methylbenzofuran (47.6 gm, 0.198 mol) is treated with several volumes of pyridine hydrochloride at 200° C. for about 6 hours to cleave the methyl ether moiety to the free hydroxyl group. Three volumes of water are added to the cooled reaction mixture and the system is extracted twice with ether. The ether extracts are combined, washed once with water and then dried over sodium sulfate. Removal of solvent by rotary evaporation affords the desired product, 2-(3-hydroxyphenyl)-3-methylbenzofuran. 2-(3-hydroxyphenyl)-3-methylbenzofuran (22.4 gm 0.1 mol) is dissolved in 100 mL of methanol in a 250 ml round bottom flask under an atmosphere of argon. To this well stirred solution is added sodium methoxide (0.54 gm, 0.01 mol). Glycidol (Aldrich, 8.14 gm, 0.11 mol) is added and the system is gradually heated and held at reflux for 18 hours. The solution is neutralized with methanesulfonic acid. The solvent is removed by rotary evaporation. The resulting product is heated on a Kugelrohr apparatus at 200° C. under a vacuum of 1 mm Hg, to remove any 3-methoxy-1,2-propanediol by-product, affording 2-[3-(2,3-dihydroxypropoxy)phenyl]-3-methylbenzofuran having the structure: ##STR55## |
Here is a chemical reaction formula: Reactants are m3:C1C(O1)CO, amount is: 0.0 ;m4:CS(=O)(=O)O, amount is: 0.0 MOLE;m2:C[O-].[Na+], amount is: 0.0 ;m1_m5:OC=1C=C(C=CC1)C=1OC2=C(C1C)C=CC=C2, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC(COC=1C=C(C=CC1)C=1OC2=C(C1C)C=CC=C2)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The ester which results from the condensation of 2'-hydroxyacetophenone and m-anisic acid is converted to 2-(3-methoxyphenyl)-3-methylbenzofuran by reductive cyclization in dioxane with a titanium tetrachloride/zinc metal catalyst according to the method of Banerji and Nayak, J. Chem. Soc., Chem. Comm., (1990), 150. The 2-(3-methoxyphenyl)-3-methylbenzofuran (47.6 gm, 0.198 mol) is treated with several volumes of pyridine hydrochloride at 200° C. for about 6 hours to cleave the methyl ether moiety to the free hydroxyl group. Three volumes of water are added to the cooled reaction mixture and the system is extracted twice with ether. The ether extracts are combined, washed once with water and then dried over sodium sulfate. Removal of solvent by rotary evaporation affords the desired product, 2-(3-hydroxyphenyl)-3-methylbenzofuran. 2-(3-hydroxyphenyl)-3-methylbenzofuran (22.4 gm 0.1 mol) is dissolved in 100 mL of methanol in a 250 ml round bottom flask under an atmosphere of argon. To this well stirred solution is added sodium methoxide (0.54 gm, 0.01 mol). Glycidol (Aldrich, 8.14 gm, 0.11 mol) is added and the system is gradually heated and held at reflux for 18 hours. The solution is neutralized with methanesulfonic acid. The solvent is removed by rotary evaporation. The resulting product is heated on a Kugelrohr apparatus at 200° C. under a vacuum of 1 mm Hg, to remove any 3-methoxy-1,2-propanediol by-product, affording 2-[3-(2,3-dihydroxypropoxy)phenyl]-3-methylbenzofuran having the structure: ##STR55## |
Here is a chemical reaction formula: Reactants are m3:[H-].[Na+], amount is: 0.0 MOLE;m4_m5_m6_m8:C(C)(=O)OCCl, amount is: 0.0 MOLE;m4_m5_m6_m8:C(C)(=O)Cl, amount is: 0.0 MOLE;m4_m5_m6_m8:C=O, amount is: 0.0 MOLE;m1_m7_m2:C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)O)C, amount is: 0.0 ;m1_m7_m2:[H-].[Na+], amount is: 11.0 MILLIMOLE,this reaction does not need reagents,Solvents are m9:O, amount is: 0.0 MOLE;m1_m7_m2:C1CCOC1, amount is: 0.0 ,Catalysts are m4_m5_m6_m8:[Cl-].[Cl-].[Zn+2], amount is: 0.0 MOLE.Products are 0:C(C)(=O)O.OCO[C@@H]1CC2=CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]2(CC1)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of dehydroepiandrosterone (2.88 g, 10 mmol) in THF (100 mL) is added sodium hydride (11 mmol, 60% in oil) at room temperature under an argon atmosphere. When all the sodium hydride has reacted, chloromethyl acetate (prepared from acetyl chloride and formaldehyde (or derivative) using ZnCl2 as catalyst) is added and the mixture is heated for a few hours. After cooling, the mixture is poured into water and extracted with ethyl acetate. The organic phase is then washed with water, dried, filtered and evaporated to dryness to give the desired compound. |
Here is a chemical reaction formula: Reactants are m4:CN1C(NC(C=2NC=NC12)=O)=O, amount is: 0.0 ;m3:C(C)OCOCC, amount is: 0.0 ;m1_m5_m2:C1(=CC=C(C=C1)S(=O)(=O)Cl)C, amount is: 0.0 ;m1_m5_m2:C(C)(=O)[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)OCN1C=NC=2N(C(NC(C12)=O)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 52.5 g (0.28 mol) of p-toluenesulfonyl chloride were initially introduced into 50 ml of dimethylformamide and 22.6 g (0.29 mol) of sodium acetate were introduced with stirring and ice-cooling. The mixture was subsequently stirred for one hour, treated with 39.1 g of formaldehyde diethyl acetal and again subsequently stirred for one hour. 41.5 g of 3-methylxanthine were then introduced and the reaction mixture was heated at 90° C. for 2 hours. After cooling to 10° C., the precipitated product was filtered off with suction, washed with a little dimethylformamide and washed with demineralized water until chloride-free. The crude product obtained was recrystallized from dimethylformamide. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C1=CC=CC=C1)N1C(=O)N(C=2N=CN(C2C1=O)COCC)C, 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:Cl.C(C1=CC=CC=C1)N1C(=O)N(C=2N=CNC2C1=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The unpurified 1-benzyl-7-ethoxymethyl-3-methylxanthine was treated with 1000 ml of 5N hydrochloric acid and stirred at 60° C. for 6 hours. The precipitated solid was filtered off with suction, washed with ethanol and dried under reduced pressure (164 g). It was possible from the mother liquor, after concentrating to approximately 50%, to isolate a further 35 g of the desired product. |
Here is a chemical reaction formula: Reactants are m2:Cl, amount is: 0.0 MOLE;m1:CN1C(N(C(C=2NC=NC12)=O)CCCCP(OCC)(OCC)=O)=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:CN1C(N(C(C=2NC=NC12)=O)CCCCP([O-])([O-])=O)=O.[NH4+].[NH4+], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5.2 g (0.0125 mol) of diethyl [4-(3-methylxanthin-1-yl)butyl]phosphonate were heated under reflux with 30 ml of 20% strength hydrochloric acid for 4 hours. The hydrochloric acid was evaporated and the oily residue was dried over potassium hydroxide in a desiccator. The phosphonic acid formed was then treated with a methanolic ammonia solution, the solvent was evaporated and the residue was crystallized from a methanol/diisopropyl ether mixture. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C1=CC=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)C, amount is: 0.05900000035762787 MOLE;m0_m1_m2:BrCCCCCP(OCC)(=O)OCC, amount is: 0.07000000029802322 MOLE,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)N1C=NC=2N(C(N(C(C12)=O)CCCCCP(OCC)(OCC)=O)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 7-benzyl-3-methylxanthine (0.059 mol) and diethyl 5-bromopentanephosphonate (0.07 mol) analogously to Example 23. |
Here is a chemical reaction formula: Reactants are m6_m4_m5_m2:C#C, amount is: 0.0 MOLE;m1_m3:C1(=CC=CC=C1)C(CO)C#C[Si](C)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6_m4_m5_m2:C(C)O, amount is: 0.0 ;m6_m4_m5_m2:O, amount is: 0.0 ;m1_m3:C(C)O, amount is: 0.0 MOLE,Catalysts are m6_m4_m5_m2:[N+](=O)([O-])[O-].[Ag+], amount is: 0.0 .Products are 0:C1(=CC=CC=C1)C(CO)C#C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Phenyl-4-trimethylsilyl-but-3-yn-1-ol (Chem. Ber. (1988), 121, 1315-1320) (7.8 g) was dissolved in ethanol and the solution was cooled to -5° C. A solution of silver nitrate (8.9 g) in ethanol (60 ml) and water (21 ml) was added dropwise to the acetylene solution such that the temperature remained below 5° C. This precipitated the acetylene as the silver complex. A solution of potassium cyanide (17 g) in water (30 ml) was added dropwise to the stirred acetylene mixture and the resulting mixture was stirred at room temperature for 30 minutes. The mixture mainly dissolved and was diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4) and evaporated. The residue was purified on silica using 10% ethyl acetate in hexane as eluant to afford the title compound (5 g) as a colourless oil. |
Here is a chemical reaction formula: Reactants are m2:N1=C(C=CC=C1C)C, amount is: 0.0 ;m1_m4:C1(=CC=CC=C1)C(C#C)O, amount is: 0.0 ;m3:FC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:ClCCl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OCC#CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-Phenyl-2-propyn-1-ol (7 g) was dissolved in dichloromethane at 0° C. under nitrogen. 2,6-Lutidine (6.17 ml) was added to the solution followed by dropwise addition of tert-butyldimethylsilyl trifluoromethane sulfonate (12.16 ml); the resulting solution was stirred overnight at room temperature. The dichloromethane was washed with water (2×), brine and dried (MgSO4) and solvent removed in vacuo. The residue was purified on flash silica using 100% petrol moving to 5% ethyl acetate/petrol, to afford the title compound as a yellow oil (10.31 g). |
Here is a chemical reaction formula: Reactants are m3:C[Li], amount is: 0.0 ;m1_m4:FC(C=1C(=CC=CC1)C=O)(F)F, amount is: 0.0 ;m2:ICCl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:O1CCCC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC(C1=C(C=CC=C1)C1OC1)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: α,α,α-trifluoro-o-tolualdehyde (3 g) was dissolved in anhydrous tetrahydrofuran and cooled to -78° C., iodochloromethane (1.38 ml) was then added, followed by methyllithium (1.5M complexed with lithium bromide) (12 ml) added over 5 minutes. The reaction was left to warm up to room temperature overnight. The reaction was quenched using saturated ammonium chloride solution and extracted using diethyl ether (2×50 ml). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to afford a brown oil. Purification on flash silica eluted with 100% hexane up to 5% EtOAC in hexane afforded a colourless oil (1.1 g). 1H NMR (250 MHz, CDCl3) δ2.61-2.71 (1H, dd), 3.14-3.25 (1H, dd), 4.17-4.27 (1H, m), 7.33-7.70 (5H, m). |
Here is a chemical reaction formula: Reactants are m1:Cl.OCC=1N=CNC1, amount is: 0.0 ;m2:C1(=CC=C(C=C1)S(=O)(=O)Cl)C, amount is: 0.0 ;m3:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OCC=1N=CN(C1)S(=O)(=O)C1=CC=C(C=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Hydroxymethylimidazole hydrochloride (10 g) was suspended in dichloromethane (200 ml). ρ-Toluenesulfonyl chloride (15.58 g) was added and triethylamine (25.8 ml) was added dropwise to the stirred reaction mixture which was allowed to stir at room temperature overnight. The mixture was washed with water (2×100 ml) and brine (1×100 ml) and the organic layer was dried and evaporated to leave a clear oil which was recrystallised from ethyl acetate/hexane to afford the title compound as a white crystalline solid (15 g, 80%). 1H NMR (360 MHz, CDCl3) δ2.44 (3H, s), 4.55 (2H, s), 7.21 (1H, s), 7.35 (2H, d, J=8.0 Hz), 7.62 (2H, d, J=8.0 Hz 7.98 (1H, s). MS (CI+) m/z 253 (M+H, 100%). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=CC=C(C(=O)CCC(=O)O)C=C1, amount is: 0.0 ;m1_m3_m2:O.NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1CCC(NN1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-(4-chlorobenzoyl)propionic acid (20 g) in absolute ethanol (200 ml) was added 5 g of hydrazine monohydrate. A thick solid was formed which dissolved after heating. The resulting solution was refluxed for 3 h, cooled and the solid formed filtered and dried to yield 16 g (80%) of 6-(4-chlorophenyl)-4,5-dihydropyridazinone. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:ClC1=CC=C(C(=O)C(C(=O)O)C)C=C1, amount is: 0.0 ;m1_m4_m2_m3:C(C)(=O)[O-].[Na+], amount is: 0.0 ;m1_m4_m2_m3:Cl.C(C)(C)(C)NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:C(CCC)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1CCC(N(N1)C(C)(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-chlorobenzoylpropionic acid (4.24 g) in n-butanol (150 ml) was added anhydrous sodium acetate (1.54 g) and t-butylhydrazine hydrochloride (2.75 g) portionwise at room temperature. The resulting mixture was refluxed for 9 hours distilling off 65 ml of n-butanol during that time. The resulting mixture was cooled and poured into water (500 ml) and extracted with methylene chloride (3×150 ml). The combined organic layers were washed with 2% aqueous sodium hydroxide (3×100 ml), water (2×100 ml), 2% aqueous hydrochloric acid (3×100 ml), and water (1×100 ml), dried and evaporated under vacuum yielding 1.71 g of the expected product. |
Here is a chemical reaction formula: Reactants are m1_m4:CC1=CC=C(C(=O)CCC(=O)O)C=C1, amount is: 0.0 ;m3:ClCl, amount is: 0.0 MOLE;m2:[Cl-].[Al+3].[Cl-].[Cl-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=C(C(=O)CCC(=O)O)C=C(C1C)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 3-(4-methylbenzoyl)propionic acid (7.5 g) and methylene chloride (250 ml) was added slowly portionwise aluminum chloride (15 g) at 0° C. After the addition was completed chlorine gas was bubbled in slowly at 0° C. After 6 hours the reaction mixture was poured into a mixture of hydrochloric acid and ice and extracted with methylene chloride (3×150 ml), the combined organic layers were washed with water, dried and evaporated under vacuum yielding 3-(3,5-dichloro-4-methylbenzoyl)propionic acid as a yellow solid (4.5 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m5:C(C#CCO)O, amount is: 0.0 ;m2:O1CCCC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m5:CCOCC, amount is: 0.0 ;m4:CCOCC, amount is: 0.0 MOLE,Catalysts are m1_m3_m5:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 .Products are 0:O1C(CCCC1)OCC#CCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 5.0 g of 2-butyne-l,4-diol and 10 milligrams of p-toluenesulfonic acid and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC1=CC=C(C=C1)C=1CCC(NN1)=O, amount is: 0.0 ;m1_m2_m3:C(C)(=O)O, amount is: 0.0 ;m1_m2_m3:BrBr, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1C=CC(NN1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 6-(4-chlorophenyl)-4,5-dihydropyridazinone (11.75 g) and glacial acetic acid (100 ml) was added dropwise 3 ml of bromine and the mixture was heated at 60°-70° C. for 3 h. The resulting mixture was cooled and slowly poured into 400 ml of cold water. The resulting white solid was filtered and dried to yield 10.83 g (89%) of 6-(4-chlorophenyl)pyridazinone. |
Here is a chemical reaction formula: Reactants are m1_m4_m5:ClC1(C(C(C1)(F)F)(F)Cl)Cl, amount is: 0.0 ;m2_m3:O, amount is: 0.0 ;m2_m3:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m5:CCOCC, amount is: 0.0 ;m1_m4_m5:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1(C(C=C1Cl)(F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1,1,2 trichloro-2,3,3-trifluorocyclobutane (55.5 g) in 100 ml of anhydrous ether, triethylamine (40 ml) was added dropwise over 30 min at room temperature, and the mixture was stirred overnight at ambient temperature. The mixture was then stirred with 120 ml H2O and 7.5 ml of concentrated HCl. The ether layer was washed with H2O (100 ml), brine (100 ml), dried over anhydrous MgSO4, and evaporated in vacuo. The residue was distilled fractionally atmospheric pressure from 64°-68° C. to yield 36 g (79%) of a colorless liquid as pure product. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC(C(C(=O)O)(F)F)(C(=O)O)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:O1CCOCC1, amount is: 0.0 ,Catalysts are m1_m2_m3:[Zn], amount is: 0.0 .Products are 0:FC(C(=O)O)(C(C(=O)O)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirring solution of the chlorotrifluorosuccinic acid (part b) (24.5 g) in 200 ml dioxane was added portionwise zinc metal (85 g) and the mixture was stirred at ambient temperature for 10 hours to yield a viscous liquid which was decanted from the unreacted zinc. Most of the dioxane was evaporated in vacuo. The residue was dissolved in 100 ml H2O and a solution of 7.7 ml of concentrated H2SO4 in 25 ml of water was added. The solution was extracted with ether (3×100 ml) and dried over anhydrous MgSO4. The organic layer was stripped to yield 8.3 g (32%) of the product as a crystalline solid. |
Here is a chemical reaction formula: Reactants are m2:O, amount is: 0.0 MOLE;m1_m4_m3:C(C1=CC=CC=C1)(=O)CCCC(=O)O, amount is: 0.0 ;m1_m4_m3:NN, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:CCOCC, amount is: 0.0 ;m1_m4_m3:C1(=CC=CC=C1)C, amount is: 0.0 ;m6:C1(=CC=CC=C1)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)C1=CC=CC(N=N1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 10 g (0.052 mole) of 4-benzoylbutyric acid in 300 ml of toluene, hydrazine was added in one portion and the reaction was heated to reflux until all water had ceased to azeotrope. The reaction mixture was cooled and the toluene was stripped off in vacuo. The residue was dissolved in 200 ml Et2O and washed with H2O (100 ml) and brine (100 ml). The ether extract was dried over anhydrous MgSO4, filtered and stripped to yield an orange semisolid which was triturated with ether to yield 3.8 g (39%) of the desired product as a yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m6_m2_m5:[H-].[Na+], amount is: 0.0 ;m1_m6_m2_m5:ClC=1C=C2CCC(C2=CC1)=O, amount is: 0.0 ;m4:COC(OC)=O, amount is: 0.0 ;m3:[H][H], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m6_m2_m5:C(OC)COC, amount is: 0.0 ;m1_m6_m2_m5:C(OC)COC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of sodium hydride (2.4 g, 60% in mineral oil, 0.06 mole) and 50 ml dry dimethoxyethane, 5-chloroindanone (50 g, 0.03 mole) in 50 ml dimethoxyethane was added dropwise at room temperature. The mixture was stirred at room temperature until hydrogen evolution ceased. Then dimethylcarbonate (27 g, 0.3 mole) was added dropwise at room temperature and the reaction was heated to 60° C. for one hour. The reaction was cooled to room temperature, quenched with 100 ml H2O, acidified to pH 5 with concentrated HCl and extracted with ethyl ether (3×100 ml). The ether extract was washed with brine (100 ml), dried over anhydrous MgSO4 and stripped to yield 3.0 g (45%) of the desired product as a tan solid. |
Here is a chemical reaction formula: Reactants are m1:P(=O)(Cl)(Cl)Cl, amount is: 0.0 ;m3:ClC1=CC=C(C=C1)CC(=O)O, amount is: 0.0 ;m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 MOLE;m2:CN(C)C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C(C=O)=CN(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phosphorus oxychloride (92 g) was added dropwise to stirred DMF (78 ml) between 10°-15° C. To the resulting slurry was added 4-chlorophenylacetic acid (34.12 g). The resulting mixture was stirred at room temperature for one half hour and then heated to 70°-80° C. during 5.5 hours, during which time the mixture became effervescent. The reaction mixture was cooled and poured slowly onto cracked ice. The resulting suspension was brought to pH 10 with solid potassium carbonate. Ice was added intermittently during this addition to maintain the temperature below 15° C. Toluene (150 ml) was added and the resulting mixture heated at 100° C. for one hour. The mixture was cooled and allowed to stand overnight. The two resulting layers were separated and the aqueous layer extracted with toluene (2×100 ml). The combined organic layers were washed with water (5×200 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo and the resulting yellow solid was triturated with hexane to yield 26 g of 2-(4-chlorophenyl)-3-dimethylaminopropenal as a tan solid mp. 120°-125° C. |
Here is a chemical reaction formula: Reactants are m3:ClC1=CC=C(C=C1)C(C=O)=CN(C)C, amount is: 0.0 MOLE;m1_m5_m2:C[O-].[Na+], amount is: 0.0 ;m1_m5_m2:C(#N)CC(=O)N, amount is: 0.0 ;m4:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 ;m1_m5_m2:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To solution of sodium methoxide (7.52 g) in methanol (130 ml) was added cyanoacetamide (5.84 g) followed by 2-(4-chlorophenyl)-3-dimethylaminopropenal and the resulting suspension was refluxed overnight. During this time a yellow solid was formed. The mixture was cooled to room temperature and glacial acetic acid (50 ml) was added followed by water (100 ml). The resulting yellow orange solid was filtered off, washed several times with water and dried to yield 8.1 g of 3-cyano-5-(4-chlorophenyl)-2-pyridinone. |
Here is a chemical reaction formula: Reactants are m4:C(C)(=O)OCC, amount is: 0.0 MOLE;m3_m5:C(C=CC1=CC=CC=C1)(=O)Cl, amount is: 0.0 ;m1_m6_m2:ClC1=CC=C(N)C=C1, amount is: 0.0 ;m1_m6_m2:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m5:C1(=CC=CC=C1)C, amount is: 0.0 ;m1_m6_m2:C1(=CC=CC=C1)C, amount is: 0.0 ;m7:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)NC(C=CC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 4-chloroaniline (16.2 g), toluene (120 ml), and pyridine (11 ml) at 0° C., cinnamoyl chloride (20.0 g) in 120 ml of toluene was added dropwise. After stirring 15 minutes at 0° C. the reaction mixture was poured into a mixture of ethyl acetate: water (250 ml:250 ml). The organic layer was separated and extracted with 5% aqueous HCl (3×250 ml), water (1×250 ml), 5% aqueous sodium bicarbonate (3×250 ml), dried over anhydrous sodium sulfate and yielding the amide as a white solid. |
Here is a chemical reaction formula: Reactants are m1_m5:[H-].[Na+], amount is: 0.0 ;m3:BrCC#CCC, amount is: 0.0 ;m2:N1C(C=CC2=CC=CC=C12)=O, amount is: 0.0 ;m4:[Cl-].[NH4+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:CN(C)C=O, amount is: 0.0 ;m6_m0:CCCCCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=C2C=CC(N(C2=CC=C1)CC#CCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of NaH (60% in mineral oil, 700 mg) in dry DMF (100 ml) at 0° C. was added the preceding quinolinone (2.05 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (1.6 g) dropwise. The resulting mixture was kept at 0° C. for one half hour and poured into saturated aqueous ammonium chloride (200 ml). The aqueous suspension was extracted with ether (3×100 ml), the combined ether layers washed with brine and dried, yielding the crude product. Triuration with hexane yielded the product as a yellow solid (1 g). |
Here is a chemical reaction formula: Reactants are m4:[Cl-].[NH4+], amount is: 0.0 MOLE;m1_m2_m3_m6_m5:ClC1=CC=C(C=C1)C(C=O)=CN(C)C, amount is: 0.0 ;m1_m2_m3_m6_m5:NC(=O)N, amount is: 0.0 ;m1_m2_m3_m6_m5:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m6_m5:C(C)O, amount is: 0.0 ;m1_m2_m3_m6_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1C=NC(NC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-(4-chlorophenyl)dimethylaminopropenal (Example 145a) (5.13 g), urea (2.4 g), concentrated HCl (10 ml), water (4 ml) and ethanol (150 ml) was refluxed for 4 hours. After cooling to room temperature concentrated ammonium chloride was added until the pH was 7. The resulting yellow solid was filtered off and dried yielding 1.5 g of 5-(4-chlorophenyl)-2-pyrimidinone. |
Here is a chemical reaction formula: Reactants are m4:[Cl-].[NH4+], amount is: 0.0 ;m2:N1C(C=CC=C1)=O, amount is: 0.0 ;m5_m0:CCCCCC, amount is: 0.0 MOLE;m1_m6:[H-].[Na+], amount is: 0.0 ;m3:BrCC#CCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1C=NC(N(C1)CC#CCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of NaH (60% in mineral oil, 340 mg) in dry DMF (75 ml) at 0° C. was added the preceding pyridinone (1.0 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (750 mg) dropwise. The resulting mixture was kept at 0° C. for one half hour and poured into saturated aqueous ammonium chloride (200 ml). The aqueous suspension was extracted with ether (3×100 ml), the combined ether layers washed with brine and dried, yielding the crude product. Trituration with hexane yielded the product as a yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=CC=C(C=C1)C=1C=CC(NN1)=O, amount is: 0.0 ;m1_m3_m2:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1C=CC(NN1)=S, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3.0 g of 6-(4-chlorophenyl)-pyridazinone, 50 ml of dry pyridine and 3.2 g of phosphorus pentasulfide was refluxed for 1 hour, evaporated to dryness and extracted with 200 ml of ether. The ether extract was washed with water (3×100 ml), brine (100 ml), dried over magnesium sulfate and evaporated to yield 3.0 g of 6-(4-chlorophenyl)-pyridazinthione as a yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=CC=C(C(=O)NN)C=C1, amount is: 0.0 ;m1_m3_m2:ClCC(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:O1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCC(=O)NNC(C1=CC=C(C=C1)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of p-chlorobenzoic hydrazide (11.2 g) in dioxane (100 ml) was added chIoroacetyl chloride (6 ml). The resulting mixture was refluxed for three hours, cooled to room temperature and filtered. The resulting solid was washed with ethyl ether and dried to yield N'-chloroacetyl-4-chlorobenzoic hydrazide as white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:BrCC(=O)C1=CC=C(C=C1)Cl, amount is: 0.0 ;m1_m2_m3:COC(=S)NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C1=NNC(SC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-bromo-p-chloroacetophenone (9.16 g), methoxythiocarbonylhydrazine (13.0 g) and acetonitrile (75 ml) was refluxed overnight and then cooled and filtered. The light yellow solid was washed with hexane and dried yielding 5-(4-chlorophenyl)-3H,6H-1,3,4-thiadiazin-2-one (4.3 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=CC=C(C(=O)CCC(=O)O)C=C1, amount is: 0.0 ;m1_m3_m2:CNN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1CCC(N(N1)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a 250 ml flask equipped with magnetic stirrer and reflux condenser was charged 10 g of 3-(4-chlorobenzoyl)-propionic acid, 250 ml of absolute ethanol, and 2.5 ml of methyl hydrazine. The reaction was refluxed for 3 hours and cooled to yield a solid which was collected by vacuum filtration, washed with 50 ml of hexane, and air dried. Isolated 9.5 g of product as a white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=CC=C(C=O)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(CCC(=O)C)(=O)O, amount is: 0.0 ;m1_m2_m3_m4:N1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=CC(=O)CCC(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a dry 250 ml flask equipped with a magnetic stirrer, Dean-Stark trap, and reflux condenser was charged 15 g of 4-chlorobenzaldehyde, 12.4 g levulenic acid, 5.7 ml of piperidine, and 100 ml of toluene. The reaction was refluxed for 3 hours, after which no water was observed to azeotrope from the solution. The reaction was cooled and stripped to yield a reddish-brown liquid which was triturated with hexane to yield 11.2 g of product as a yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:[N+](=O)([O-])C=1C(=C(C(=O)[O-])C=CC1OC)C, amount is: 0.0 ;m1_m3_m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a 500 ml erlenmeyer flask with magnetic stirrer was charged 10.3 g of 3-nitro-4-methoxy-methylbenzoate, 400 ml tetrahydrofuran, and 3.2 g of 86% potassium hydroxide. The reaction was stirred for 12 hours at ambient temperature, after which the resulting solid was collected by vacuum filtration and washed with 2×100 ml of ethyl ether. The solid was dissolved in 200 ml of water and acidified to pH 4 with 6N hydrochloric acid. The resulting precipitate was collected by vacuum filtration, washed with 200 ml water, and dried overnight in vacuo at 30° C. Isolated 7.4 g of product as a white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS(=O)(=O)C)C=C1, amount is: 0.0 ;m1_m2_m3_m4:O.NN, amount is: 0.0 ;m1_m2_m3_m4:C(C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C)=NN)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-chloro-4'-methylsulfonylmethylbenzophenone (10.0 g) and hydrazine monohydrate (4.9 g) were added to ethanol (200 ml) and acetic acid (10 ml), and the mixture was stirred for 6 hours under reflux. The reaction mixture was concentrated, and the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the desired product (10.0 g, melting point: 52° to 54° C., yield: 97%) |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m1_m2_m3:ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C)=NN)C=C1, amount is: 0.0 ;m1_m2_m3:ClS(=O)(=O)N=C=O, amount is: 0.0 ;m1_m2_m3:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m0:CCCCCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C)=NNC(=O)N)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-chloro-4'-methylsulfonylmethylbenzophenone-hydrazone (1.3 g) and chlorosulfonyl isocyanate (0.63 g) were added to ethyl acetate (100 ml), and the mixture was stirred for one hour at room temperature. Then, water (100 ml) was added, and the mixture was further stirred for 16 hours at room temperature. The reaction mixture was subjected to liquid separation, and the ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residual solid was washed with a solvent mixture of ethyl acetate:n-hexane=4:1, to obtain the desired product (1.2 g, melting point: 189° to 191° C., yield: 80%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:BrCC1=CC=C(C(=O)C2=CC=C(C=C2)Cl)C=C1, amount is: 0.0 ;m1_m2_m3:CS(=O)[O-].[Na+], amount is: 0.0 ;m1_m2_m3:CN(C=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS(=O)(=O)C)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-bromomethyl-4'-chlorobenzophenone (3.1 g) and sodium methanesulfinate (1.5 g) were added to N,N-dimethylformamide (50 ml), and the mixture was stirred for 16 hours at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residual solid was washed with n-hexane to obtain the desired product (2.8 g, melting point: 164° to 166° C., yield: 90%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(C)Br, amount is: 0.0 ;m1_m2_m3_m4:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSCC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-chloro-4'-mercaptomethylbenzophenone (16.0 g), ethyl bromide (7.4 g) and potassium hydroxide (4.3 g) were added to methanol (250 ml), and the mixture was stirred for 30 minutes under reflux. The reaction mixture was cooled to room temperature and then concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1) to obtain the desired product 14.0 g, melting point: 33° to 34° C., yield: 79%). |
Here is a chemical reaction formula: Reactants are m4:FC(F)Cl, amount is: 0.0 MOLE;m5:ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS)C=C1, amount is: 0.0 MOLE;m1_m2_m3_m6:ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS)C=C1, amount is: 0.0 ;m1_m2_m3_m6:[OH-].[K+], amount is: 0.0 ;m1_m2_m3_m6:O1CCOCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m6:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSC(F)F)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-chloro-4'-mercaptomethylbenzophenone (14.7 g) and potassium hydroxide (15 g) was added to a solvent comprising dioxane (100 ml) and water (100 ml). Difluoromethyl chloride was blown into this solution at 60° C. until the starting material 4-chloro-4'-mercaptomethylbenzophenone disappeared. The reaction product was cooled to room temperature and then subjected to filtration. The organic layer as the filtrate was dried over anhydrous magnesium sulfate add concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the desired product (6.4 g, melting point: 34° to 35° C., yield: 36%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:BrCC1=CC=C(C(=O)C2=CC=C(C=C2)Cl)C=C1, amount is: 0.0 ;m1_m2_m3:CS.[Na], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-bromomethyl-4'-chlorobenzophenone (3.1 g) and 15% methylmercaptan-sodium aqueous solution (5.6 g) were added to methanol (150 ml), and the mixture was stirred for 30 minutes under reflux. The reaction mixture was concentrated and extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residual solid was washed with n-hexane to obtain the desired product (2.3 g, melting point: 59° to 61° C., yield: 83%). |
Here is a chemical reaction formula: Reactants are m3_m4:I(=O)(=O)(=O)[O-].[Na+], amount is: 0.0 ;m1_m2:ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSC)C=C1, amount is: 0.0 ;m1_m2:CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS(=O)C)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-chloro-4'-methylthiomethylbenzophenone (4.2 g) was added to methanol (150 ml). Sodium periodate (3.6 g) dissolved in water (20 ml), was added to this solution, and the mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated, and water was added thereto. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residual solid was washed with n-hexane to obtain the desired product (4.1 g, melting point: 116° to 118° C., yield: 93%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:BrCCCS(=O)(=O)CC1=CC=C(C(=O)C2=CC=C(C=C2)Cl)C=C1, amount is: 0.0 ;m1_m2_m3:[H-].[Na+], amount is: 0.0 ;m1_m2_m3:CN(C(C)=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(=O)C2=CC=C(C=C2)C2S(CCC2)(=O)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(3-bromopropyl)sulfonylmethyl-4'-chlorobenzophenone (2.5 g) and 60% sodium hydride (0.3 g) were added to N,N-dimethylacetamide (70 ml), and the mixture was stirred for 16 hours at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the desired product as a slightly yellow viscous substance 1.0 g, yield: 50%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:BrCC1=CC=C(C(=O)C2=CC=C(C=C2)Cl)C=C1, amount is: 0.0 ;m1_m2_m3:[S-]C#N.[Na+], amount is: 0.0 ;m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m0:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSC#N)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-bromomethyl-4'-chlorobenzophenone (5.7 g) and sodium thiocyanate (5.5 g) were added to ethanol (50 ml), and the mixture was stirred for one hour at 60° C. The reaction mixture was concentrated, and water was added to the residue. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residual solid was washed with a solvent mixture of n-hexane:ethyl acetate=10:1 to obtain the desired product (2.2 g, melting point: 129° to 131° C., yield:42%). |
Here is a chemical reaction formula: Reactants are m1_m3:ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS(=O)(=O)C(F)(F)F)C=C1, amount is: 0.0 ;m2:[BH4-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:CO, amount is: 0.0 MOLE;m1_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C(F)(F)F)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-chloro-4'-trifluoromethylsulfonylmethylbenzophenone (5.5 g) was dispersed in methanol (200 ml). Sodium borohydride was gradually added thereto at room temperature with stirring, and the mixture was further stirred overnight at room temperature. After completion of the reaction, methanol was distilled off under reduced pressure. The residue was extracted with ethyl acetate (250 ml). The extract was washed with water and dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the desired product as a white powder (4.2 g, melting point: 113° to 115° C., yield: 77%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)CC)O)C=C1, amount is: 0.0 ;m1_m2_m3_m4:S(=O)(Cl)Cl, amount is: 0.0 ;m1_m2_m3_m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CN(C=O)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)CC)Cl)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-chloro-4'-ethane sulfonylmethylbenzhydrol (6.0 g), thionyl chloride (5.4 g), toluene (200 ml) and a catalytic amount of N,N-dimethylformamide were mixed and gradually heated with stirring to a refluxing temperature. The mixture was stirred for 4 hours under reflux and then left to cool. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the desired product as a slight yellow viscous substance (4.6 g, nD20 : 1.6044, yield: 75%). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=CC=C(C(=O)CCC(=O)O)C=C1, amount is: 0.0 ;m1_m3_m2:O.NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1CCC(NN1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-(4-chlorobenzoyl)propionic acid (20 g) in absolute ethanol (200 ml) was added 5 g of hydrazine monohydrate. A thick solid was formed which dissolved after heating. The resulting solution was refluxed for 3 h, cooled and the solid formed filtered and dried to yield 16 g (80%) of 6-(4-chlorophenyl)-4,5-dihydropyridazinone. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:ClC1=CC=C(C(=O)C(C(=O)O)C)C=C1, amount is: 0.0 ;m1_m4_m2_m3:C(C)(=O)[O-].[Na+], amount is: 0.0 ;m1_m4_m2_m3:Cl.C(C)(C)(C)NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:C(CCC)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1CCC(N(N1)C(C)(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-chlorobenzoylpropionic acid (4.24 g) in n-butanol (150 ml) was added anhydrous sodium acetate (1.54 g) and t-butylhydrazine hydrochloride (2.75 g) portionwise at room temperature. The resulting mixture was refluxed for 9 hours distilling off 65 ml of n-butanol during that time. The resulting mixture was cooled and poured into water (500 ml) and extracted with methylene chloride (3×150 ml). The combined organic layers were washed with 2% aqueous sodium hydroxide (3×100 ml), water (2×100 ml), 2% aqueous hydrochloric acid (3×100 ml), and water (1×100 ml), dried and evaporated under vacuum yielding 1.71 g of the expected product. |
Here is a chemical reaction formula: Reactants are m3:ClCl, amount is: 0.0 MOLE;m2:[Cl-].[Al+3].[Cl-].[Cl-], amount is: 0.0 ;m1_m4:CC1=CC=C(C(=O)CCC(=O)O)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=C(C(=O)CCC(=O)O)C=C(C1C)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 3-(4-methylbenzoyl)propionic acid (7.5 g) and methylene chloride (250 ml) was added slowly portionwise aluminum chloride (15 g) at 0° C. After the addition was completed chlorine gas was bubbled in slowly at 0° C. After 6 hours the reaction mixture was poured into a mixture of hydrochloric acid and ice and extracted with methylene chloride (3×150 ml), the combined organic layers were washed with water, dried and evaporated under vacuum yielding 3-(3,5-dichloro-4-methylbenzoyl)propionic acid as a yellow solid (4.5 g). |
Here is a chemical reaction formula: Reactants are m1:C(C#CCO)O, amount is: 0.0 ;m2:O1CCCC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:CCOCC, amount is: 0.0 MOLE;m4:CCOCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O1C(CCCC1)OCC#CCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic add and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC1=CC=C(C=C1)C=1CCC(NN1)=O, amount is: 0.0 ;m1_m2_m3:C(C)(=O)O, amount is: 0.0 ;m1_m2_m3:BrBr, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1C=CC(NN1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 6-(4-chlorophenyl)-4,5-dihydropyridazinone (11.75 g) and glacial acetic acid (100 ml) was added dropwise 3 ml of bromine and the mixture was heated at 60°-70° C. for 3 h. The resulting mixture was cooled and slowly poured into 400 ml of cold water. The resulting white solid was filtered and dried to yield 10.83 g (89%) of 6-(4-chlorophenyl)pyridazinone. |
Here is a chemical reaction formula: Reactants are m2_m3:O, amount is: 0.0 ;m2_m3:Cl, amount is: 0.0 ;m1_m4_m5:ClC1(C(C(C1)(F)F)(F)Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m5:CCOCC, amount is: 0.0 ;m1_m4_m5:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1(C(C=C1Cl)(F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1,1,2 trichloro-2,3,3-trifluorocyclobutane (55.5 g) in 100 ml of anhydrous ether, triethylamine (40 ml) was added dropwise over 30 min at room temperature, and the mixture was stirred overnight at ambient temperature. The mixture was then stirred with 120 ml H2O and 7.5 ml of concentrated HCl. The ether layer was washed with H2O (100 ml), brine (100 ml), dried over anhydrous MgSO4, and evaporated in vacuo. The residue was distilled fractionally atmospheric pressure from 64°-68° C. to yield 36 g (79%) of a colorless liquid as pure product. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC(C(C(=O)O)(F)F)(C(=O)O)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:O1CCOCC1, amount is: 0.0 ,Catalysts are m1_m2_m3:[Zn], amount is: 0.0 .Products are 0:FC(C(=O)O)(C(C(=O)O)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirring solution of the chlorotrifluorosuccinic acid (part b) (24.5 g) in 200 ml dioxane was added portionwise zinc metal (85 g) and the mixture was stirred at ambient temperature for 10 hours to yield a viscous liquid which was decanted from the unreacted zinc. Most of the dioxane was evaporated in vacuo. The residue was dissolved in 100 ml H2O and a solution of 7.7 ml of concentrated H2SO4 in 25 ml of water was added. The solution was extracted with ether (3×100 ml) and dried over anhydrous MgSO4. The organic layer was stripped to yield 8.3 g (32%) of the product as a crystalline solid. |
Here is a chemical reaction formula: Reactants are m4:COC(OC)=O, amount is: 0.0 ;m3:[H][H], amount is: 0.0 MOLE;m1_m6_m2_m5:[H-].[Na+], amount is: 0.0 ;m1_m6_m2_m5:ClC=1C=C2CCC(C2=CC1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6_m2_m5:C(OC)COC, amount is: 0.0 ;m1_m6_m2_m5:C(OC)COC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of sodium hydride (2.4 g, 60% in mineral oil, 0.06 mole) and 50 ml dry dimethoxyethane, 5-chloroindanone (50 g, 0.03 mole) in 50 ml dimethoxyethane was added dropwise at room temperature. The mixture was stirred at room temperature until hydrogen evolution ceased. Then dimethylcarbonate (27 g, 0.3 mole) was added dropwise at room temperature and the reaction was heated to 60° C. for one hour. The reaction was cooled to room temperature, quenched with 100 ml H2O, acidified to pH 5 with concentrated HCl and extracted with ethyl ether (3×100 ml). The ether extract was washed with brine (100 ml), dried over anhydrous MgSO4 and stripped to yield 3.0 g (45%) of the desired product as a tan solid. |
Here is a chemical reaction formula: Reactants are m3:ClC1=CC=C(C=C1)CC(=O)O, amount is: 0.0 ;m1:P(=O)(Cl)(Cl)Cl, amount is: 0.0 ;m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 MOLE;m2:CN(C)C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C(C=O)=CN(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phosphorus oxychloride (92 g) was added dropwise to stirred DMF (78 ml) between 10°-15° C. To the resulting slurry was added 4-chlorophenylacetic acid (34.12 g). The resulting mixture was stirred at room temperature for one half hour and then heated to 70°-80° C. during 5.5 hours, during which time the mixture became effervescent. The reaction mixture was cooled and poured slowly onto cracked ice. The resulting suspension was brought to pH 10 with solid potassium carbonate. Ice was added intermittently during this addition to maintain the temperature below 15° C. Toluene (150 ml) was added and the resulting mixture heated at 100° C. for one hour. The mixture was cooled and allowed to stand overnight. The two resulting layers were separated and the aqueous layer extracted with toluene (2×100 ml). The combined organic layers were washed with water (5×200 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo and the resulting yellow solid was triturated with hexane to yield 26 g of 2-(4-chlorophenyl)-3-dimethylaminopropenal as a tan solid mp. 120°-125° C. |
Here is a chemical reaction formula: Reactants are m1_m5_m2:C[O-].[Na+], amount is: 0.0 ;m1_m5_m2:C(#N)CC(=O)N, amount is: 0.0 ;m3:ClC1=CC=C(C=C1)C(C=O)=CN(C)C, amount is: 0.0 MOLE;m4:CC(=O)OCC1=C2C=CC=CC2=C(C3=CC=CC=C31)COC(=O)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m2:CO, amount is: 0.0 ;m6:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To solution of sodium methoxide (7.52 g) in methanol (130 ml) was added cyanoacetamide (5.84 g) followed by 2-(4-chlorophenyl)-3-dimethylaminopropenal and the resulting suspension was refluxed overnight. During this time a yellow solid was formed. The mixture was cooled to room temperature and glacial acetic add (50 ml) was added followed by water (100 ml). The resulting yellow orange solid was filtered off, washed several times with water and dried to yield 8.1 g of 3-cyano-5-(4-chlorophenyl)-2-pyridinone. |
Here is a chemical reaction formula: Reactants are m1_m6_m2:ClC1=CC=C(N)C=C1, amount is: 0.0 ;m1_m6_m2:N1=CC=CC=C1, amount is: 0.0 ;m3_m5:C(C=CC1=CC=CC=C1)(=O)Cl, amount is: 0.0 ;m4:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m6_m2:C1(=CC=CC=C1)C, amount is: 0.0 ;m3_m5:C1(=CC=CC=C1)C, amount is: 0.0 ;m7:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)NC(C=CC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 4-chloroaniline (16.2 g), toluene (120 ml), and pyridine (11 ml) at 0° C., cinnamoyl chloride (20.0 g) in 120 ml of toluene was added dropwise. After stirring 15 minutes at 0° C. the reaction mixture was poured into a mixture of ethyl acetate: water (250 ml:250 ml). The organic layer was separated and extracted with 5% aqueous HCl (3×250 ml), water (1×250 ml), 5% aqueous sodium bicarbonate (3×250 ml), dried over anhydrous sodium sulfate and evaporated yielding the amide as a white solid. |
Here is a chemical reaction formula: Reactants are m3:BrCC#CCC, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ;m4:[Cl-].[NH4+], amount is: 0.0 ;m2:N1C(C=CC2=CC=CC=C12)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:CN(C)C=O, amount is: 0.0 ;m6_m0:CCCCCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=C2C=CC(N(C2=CC=C1)CC#CCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of NaH (60% in mineral oil, 700 mg) in dry DMF (100 ml) at 0° C. was added the preceding quinolinone (2.05 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (1.6 g) dropwise. The resulting mixture was kept at 0° C. for one half hour and poured into saturated aqueous ammonium chloride (200 ml). The aqueous suspension was extracted with ether (3×100 ml), the combined ether layers washed with brine and dried, yielding the crude product. Trituration with hexane yielded the product as a yellow solid (1 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m6_m5:ClC1=CC=C(C=C1)C(C=O)=CN(C)C, amount is: 0.0 ;m1_m2_m3_m6_m5:NC(=O)N, amount is: 0.0 ;m1_m2_m3_m6_m5:Cl, amount is: 0.0 ;m4:[Cl-].[NH4+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m6_m5:C(C)O, amount is: 0.0 ;m1_m2_m3_m6_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1C=NC(NC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-(4-chlorophenyl)dimethylaminopropenal (Example 145a) (5.13 g), urea (2.4 g), concentrated HCl (10 ml), water (4 ml) and ethanol (150 ml) was refluxed for 4 hours. After cooling to room temperature concentrated ammonium chloride was added until the pH was 7. The resulting yellow solid was filtered off and dried yielding 1.5 g of 5-(4-chlorophenyl)-2-pyrimidinone. |
Here is a chemical reaction formula: Reactants are m3:BrCC#CCC, amount is: 0.0 ;m2:N1C(C=CC=C1)=O, amount is: 0.0 ;m4:[Cl-].[NH4+], amount is: 0.0 ;m1_m6:[H-].[Na+], amount is: 0.0 ;m5_m0:CCCCCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m6:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1C=NC(N(C1)CC#CCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of NaH (60% in mineral oil, 340 mg) in dry DMF (75 ml) at 0° C. was added the preceding pyridinone (1.0 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (750 mg) dropwise. The resulting mixture was kept at 0° C. for one half hour and poured into saturated aqueous ammonium chloride (200 ml). The aqueous suspension was extracted with ether (3×100 ml), the combined ether layers washed with brine and dried, yielding the crude product. Trituration with hexane yielded the product as a yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=CC=C(C=C1)C=1C=CC(NN1)=O, amount is: 0.0 ;m1_m3_m2:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1C=CC(NN1)=S, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3.0 g of 6-(4-chlorophenyl)-pyridazinone, 50 ml of dry pyridine and 3.2 g of phosphorus pentasulfide was refluxed for 1 hour, evaporated to dryness and extracted with 200 ml of ether. The ether extract was washed with water (3×100 ml), brine (100 ml), dried over magnesium sulfate and evaporated to yield 3.0 g of 6-(4-chlorophenyl)-pyridazinthione as a yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=CC=C(C(=O)NN)C=C1, amount is: 0.0 ;m1_m3_m2:ClCC(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:O1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCC(=O)NNC(C1=CC=C(C=C1)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of p-chlorobenzoic hydrazide (11.2 g) in dioxane (100 ml) was added chloroacetyl chloride (6 ml). The resulting mixture was refluxed for three hours, cooled to room temperature and filtered. The resulting solid was washed with ethyl ether and dried to yield N'-chloroacetyl-4-chlorobenzoic hydrazide as white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:BrCC(=O)C1=CC=C(C=C1)Cl, amount is: 0.0 ;m1_m2_m3:COC(=S)NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C1=NNC(SC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-bromo-p-chloroacetophenone (9.16 g), methoxythiocarbonylhydrazine (13.0 g) and acetonitrile (75 ml) was refluxed overnight and then cooled and filtered. The light yellow solid was washed with hexane and dried yielding 5-(4-chlorophenyl)-3H,6H-1,3,4-thiadiazin-2-one (4.3 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=CC=C(C(=O)CCC(=O)O)C=C1, amount is: 0.0 ;m1_m3_m2:CNN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1CCC(N(N1)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a 250 ml flask equipped with magnetic stirrer and reflux condenser was charged 10 g of 3-(4-chlorobenzoyl)-propionic acid, 250 ml of absolute ethanol, and 2.5 ml of methyl hydrazine. The reaction was refluxed for 3 hours and cooled to yield a solid which was collected by vacuum filtration, washed with 50 ml of hexane, and air dried. Isolated 9.5 g of product as a white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=CC=C(C=O)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(CCC(=O)C)(=O)O, amount is: 0.0 ;m1_m2_m3_m4:N1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=CC(=O)CCC(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a dry 250 ml flask equipped with a magnetic stirrer, Dean-Stark trap, and reflux condenser was charged 15 g of 4-chlorobenzaldehyde, 12.4 g levulenic acid, 5.7 ml of piperidine, and 100 ml of toluene. The reaction was refluxed for 3 hours, after which no water was observed to azeotrope from the solution. The reaction was cooled and stripped to yield a reddish-brown liquid which was triturated with hexane to yield 11.2 g of product as a yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:[N+](=O)([O-])C=1C(=C(C(=O)[O-])C=CC1OC)C, amount is: 0.0 ;m1_m3_m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a 500 ml erlenmeyer flask with magnetic stirrer was charged 10.3 g of 3-nitro-4-methoxy-methylbenzoate, 400 ml tetrahydrofuran, and 3.2 g of 86% potassium hydroxide. The reaction was stirred for 12 hours at ambient temperature, after which the resulting solid was collected by vacuum filtration and washed with 2×100 ml of ethyl ether. The solid was dissolved in 200 ml of water and acidified to pH 4 with 6N hydrochloric acid. The resulting precipitate was collected by vacuum filtration, washed with 200 ml water, and dried overnight in vacuo at 30° C. Isolated 7.4 g of product as a white solid. |
Here is a chemical reaction formula: Reactants are m3:BrCC1=CC=C(C#N)C=C1, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE;m1_m5_m2:[H-].[Na+], amount is: 0.0 ;m1_m5_m2:N1C(NCC1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C1N(CCN1CC1=CC=C(C#N)C=C1)CC1=CC=C(C#N)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To sodium hydride (2.4 g, 60 mmol) in dimethylformamide (50 mL) at 0° C. was added imidazolin-2-one (2.6 g, 30 mmol). After stirring for 20 minutes 4-(bromomethyl)benzonitrile (13 g, 66 mmol) was added and the mixture was warmed to ambient temperature. After stirring for 1 hour the reaction was poured into water and a solid formed. The solid was filtered to give 4,4'-[(2-oxoimidazolin-1,3-diyl) bis(methylene)]-bis(benzonitrile). NMR (CDCl3) 7.65 (d,4), 7.4 (d,4), 4.45 (s,4), 3.2 (s,4) ppm. |
Here is a chemical reaction formula: Reactants are m3_m1_m2:NC(=O)N, amount is: 0.0 ;m3_m1_m2:CN(C1=CC=C(C=C1)C(C(=O)C1=CC=CC=C1)O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m1_m2:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C1=CC=C(C=C1)C=1NC(NC1C1=CC=CC=C1)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To acetic acid (2 mL) was added urea (0.6 g, 10 mmol) and 2-(4-dimethylaminophenyl)-2-hydroxy-1-phenylethanone (2.6 g, 10 mmol). After stirring for 2 hours at 120° C., the reaction was cooled to ambient temperature. The resulting solid was filtered, washed with ether, and dried in vacuo to give 4-(4-dimethylaminophenyl)-2,3-dihydro-5-phenyl-1H-imidazol-2-one; NMR (CDCl3) 10.98 (s,2), 7.5 (m,4), 7.4 (m,5), 3.18 (s,6) ppm. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O, amount is: 0.0 ;m1_m2_m3_m4:BrCC=1C=C(C#N)C=CC1, amount is: 0.0 ;m1_m2_m3_m4:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a manner similar to Preparation 1 above, 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (1.2 g, 5 mmol) was reacted with 3-(bromomethyl)benzonitrile (0.39 g, mmol) and sodium hydride (0.18 g, 5 mmol) in dimethylformamide (20 mL) to give 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile after chromatography on silica; NMR (DMSO-d6) 11.02 (s, 1), 7.4 (m,4), 7.3 (m,2), 7.2 (m,7), 4.75 (s,2) ppm. |
Here is a chemical reaction formula: Reactants are m2_m6:BrCC=1C=C(C(=O)OC)C=CC1, amount is: 0.0 ;m3:Cl, amount is: 0.0 MOLE;m1_m4_m5:C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m6:CN(C)C=O, amount is: 0.0 ;m1_m4_m5:CN(C)C=O, amount is: 0.0 ;m1_m4_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (4.76 g, 20 mmol) in 50 mL DMF was added to a suspension of Nail (0.8 g, 20 mmol) in 25 mL DMF. The suspension was stirred at ambient temperatures for 30 minutes, then heated to 50° C. for 30 minutes. A solution of methyl 3-bromomethylbenzoate (2.86 g, 12.5 mmol) in 20 mL DMF was then added and the reaction stirred for 10 min at 50° C. The mixture was poured into 1 N HCl, filtered, washed with water and dried. Chromatography on silica gel (2% EtOH in 7:3 methylene chloride/ethyl acetate) afforded 1.2 g of 3-(3-methoxycarbonylphenyl)methyl-4,5-diphenyl-1H-imidazol-2-one as a white solid. |
Here is a chemical reaction formula: Reactants are m1:C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O, amount is: 0.0 MOLE;m2:BrCC1=CC=C2C=CC(=CC2=C1)C#N, 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(#N)C=1C=C(C=CC1)CN1C(N(C(=C1C1=CC=CC=C1)C1=CC=CC=C1)CC1=CC=C2C=CC(=CC2=C1)C#N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a manner similar to Preparation 2 above, 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl) methyl]benzonitrile was reacted with 7-(bromomethyl)-naphthalene-2-carbonitrile to give 7-[[3-(3-cyanophenyl)methyl-2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl]methyl]naphthalene-2-carbonitrile; NMR (CDCl3) 8.05 (s,1), 7.9 (d,1), 7.85 (d,1), 7.55 (m,3), 7.4 (m,2), 7.2 (m,9), 7.0 (m,3), 5.1 (s,2), 4.95 (s,2) ppm. |
Here is a chemical reaction formula: Reactants are m3:C1NC(CC2=CC=CC=C12)C(=O)O, amount is: 0.0 ;m1_m2:C(C)(=O)Cl, amount is: 0.0 ;m1_m2:CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(=O)C1NCC2=CC=CC=C2C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Acetyl chloride (0.88 g) was added to methanol (100 ml) with stirring at 0° C. After 10 minutes, 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (J. Am. Chem. Soc., 1962, 48, 4487-4494) (2.0 g) was added; the reaction was allowed to warm to room temperature and stirred overnight. DMF (1 ml) was then added and stirring was then continued for a further 24 h. The solvent was removed in vacuo; dichloromethane was added and the solid thus formed was filtered off and partitioned between dichloromethane (50 ml) and saturated aqueous sodium hydrogen carbonate solution (50 ml). The organic phase was dried (magnesium sulphate), filtered, and the filtrate evaporated in vacuo to yield the title compound as a pale yellow oil (1.0 g). |
Here is a chemical reaction formula: Reactants are m2_m7:ClS(=O)(=O)O, amount is: 0.0 ;m3:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ;m9_m4:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ;m5:C1(=CC=CC=C1)C, amount is: 0.0 ;m1_m6:CS(=O)(=O)OCOC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m7:ClCCl, amount is: 0.0 ;m9_m4:ClCCl, amount is: 0.0 ;m1_m6:ClCCl, amount is: 0.0 ,Catalysts are m8:CN(C)C=O, amount is: 0.0 MOLE.Products are 0:CS(=O)(=O)OC=1C=C(C=CC1OC)S(=O)(=O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-(methanesulphonyloxy)methoxybenzene (0.822 g) in dichloromethane (15 ml) was stirred and cooled to -10° C. under a nitrogen atmosphere. A solution of chlorosulphonic acid (0.27 ml) in dichloromethane (5 ml) was then added dropwise over a period of 1 hour, maintaining the temperature below 0° C. The mixture was stirred for a further 4 hours, allowing the temperature to rise to 10° C. The mixture was evaporated to dryness in vacuo to yield an oil which was suspended in toluene (20 ml) with stirring under a nitrogen atmosphere. Oxalyl chloride (0.36 ml) was added dropwise, followed by the addition of DMF (5 drops). After stirring for 2 hours at room temperature, dichloromethane (15 ml) and oxalyl chloride (0.36 ml) were added and the reaction stirred overnight. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica, eluting with 60% ethyl acetate in hexane to furnish the title compound (0.99 g) as a white crystalline solid. |
Here is a chemical reaction formula: Reactants are m1_m2:CS(=O)(=O)OC=1C=C(C=CC1OC)S(=O)(=O)N1CCC2=CC=CC=C12, amount is: 0.0 ;m1_m2:[OH-].[Na+], 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=CC1OC)S(=O)(=O)N1CCC2=CC=CC=C12, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of N-(3-methanesulphonyloxy-4-methoxybenzenesulphonyl)-1,2-dihydroindole (1 g) and saturated aqueous sodium hydroxide solution (2 ml) was heated at 85°-90° C. for 2 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (5 ml) and water (10 ml). The aqueous phase was acidified with 2N HCl and extracted with ethyl acetate (2×10 ml). The combined organic phases were dried over magnesium sulphate and concentrated in vacuo to yield a clear oil. Purification by column chromatography eluting with dichloromethane afforded the desired product as a white solid (0.8 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m4:N1CCCC2=CC=CC=C12, amount is: 0.0 ;m1_m2_m4:COC=1C=C(C=CC1OC)S(=O)(=O)Cl, amount is: 0.0 ;m3:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:ClCCl, amount is: 0.0 ;m5:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC=1C=C(C=CC1OC)S(=O)(=O)N1CCCC2=CC=CC=C12, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1,2,3,4-Tetrahydroquinoline (0.29 ml) was added to a suspension of 3,4-dimethoxybenzene sulphonyl chloride (0.50 g) in dichloromethane (15 ml) at room temperature. Triethylamine (0.44 ml) was added and the resulting mixture stirred for 24 hours at room temperature. The reaction mixture was then diluted with dichloromethane (20 ml) and washed successively with saturated aqueous sodium hydrogen carbonate solution (10 ml), 2N hydrochloric acid (10 ml) and saturated aqueous sodium chloride solution (10 ml). Drying over magnesium sulphate and concentration in vacuo provided a yellow oil. Purification by column chromatography eluting with 30% ethyl acetate in hexane provided the title compound as a colourless oil (0.60 g) which solidified on standing. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:OC=1C=C(C=CC1OC)S(=O)(=O)N1CCC2=CC=CC=C12, amount is: 0.0 ;m1_m2_m4_m3:O(C1=CC=CC=C1)CCCBr, amount is: 0.0 ;m1_m2_m4_m3:C([O-])([O-])=O.[Cs+].[Cs+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O(C1=CC=CC=C1)CCCOC=1C=C(C=CC1OC)S(=O)(=O)N1CCC2=CC=CC=C12, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of N-(3-hydroxy-4-methoxybenzenesulphonyl)- 1,2-dihydroindole (0.2 g) and 3-phenoxypropylbromide (0.15 g) in N,N-dimethylformamide (20 ml) was treated with cesium carbonate (0.3 g) and heated at 75° C. overnight. The solvent was removed in vacuo and the residue partitioned between dichloromethane (30 ml) and water (15 ml). The organic phase was washed with brine (15 ml) then dried over magnesium sulphate and concentrated in vacuo. The residue was purified using column chromatography eluting with dichloromethane to yield the title compound as a white solid (0.25 g). |
Here is a chemical reaction formula: Reactants are m2:[H-].[Na+], amount is: 0.0 ;m3:COC=1C=C(C=CC1OC)S(=O)(=O)Cl, amount is: 0.0 ;m1_m4:C1(=CC=CC=C1)C=1NC(=O)C2=CC=CC=C2C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC=1C=C(C=CC1OC)S(=O)(=O)N1C(=O)C2=CC=CC=C2C=C1C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 3-phenylisocarbostyril (0.1 g) in N,N-dimethylformamide (2 ml) was cooled to 0° C. under an inert atmosphere. Sodium hydride (0.019 g) was added and the resulting mixture stirred at 0° C. for 5 minutes. 3,4-Dimethoxybenzenesulphonylchloride (0.107 g) was added over a 3 minute period, with continued stirring at 0° C. for a further 15 minutes. The reaction mixture was warmed to room temperature and stirred for 24 hours. The DMF was evaporated under high vacuum and the residue partitioned between ethyl acetate (2×12 ml) and water (12 ml). The combined organic phases were dried over magnesium sulphate and concentrated in vacuo to yield a yellow oil. Purification using column chromatography eluting with 50% ethyl acetate in hexane yielded an oil which was crystallized from ethyl acetate/hexane to furnish the title compound as white crystals (0.089 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m8_m5:COC=1C=C(C=CC1OC)S(=O)(=O)N1CC2=CC=CC(=C2C1)Br, amount is: 0.0 ;m1_m2_m3_m8_m5:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m3_m8_m5:C(#C)C1=NC=CC=C1, amount is: 0.0 ;m4_m6:C(#C)C1=NC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m8_m5:CN(C=O)C, amount is: 0.0 ;m7:C(C)(=O)OCC, amount is: 0.0 MOLE,Catalysts are m1_m2_m3_m8_m5:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl, amount is: 0.0 MOLE;m4_m6:[Pd], amount is: 0.0 MOLE.Products are 0:COC=1C=C(C=CC1OC)S(=O)(=O)N1CC2=CC=CC(=C2C1)C#CC1=NC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(3,4-Dimethoxybenzenesulphonyl)-4-bromoisoindoline (0.19 g), triethylamine (0.10 ml), 2-ethynylpyridine(0.06 g) and bis (triphenylphosphine)palladium(II)chloride (10%) in anhydrous N,N-dimethylformamide(2 ml) were stirred together under an inert atmosphere and heated to 90° C. After 20 hours further 2-ethynylpyridine(0.12 g) and palladium catalyst (20%) were added and heating continued for 3 days. The reaction mixture at room temperature was diluted with ethyl acetate, filtered through a pad of silica and the filtrate evaporated in vacuo to yield a yellow residue. Purification by column chromatography, eluting with a 20-100% ethyl acetate in hexane gradient afforded the title compound (25 mg). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:N1=CC=C(C=C1)NC1=NOC2=C1C=CC=C2, amount is: 0.0 ;m1_m2_m3:BrCC(=O)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Br.COC(CN1C=CC(C=C1)=NC1=NOC2=C1C=CC=C2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3-(4-pyridinylamino)-1,2-benzisoxazole (0.9 g, 4.3 mmol) and methyl bromoacetate (0.44 mL, 1.1 eq) in acetonitrile (25 mL) was heated at reflux for one hour. The mixture was then allowed to cool to room temperature and the precipitated product was collected by filtration. The white solid was washed with diethyl ether and dried under vacuum to provide the title compound (1.1 g, 70%), mp 235-236° C. |
Here is a chemical reaction formula: Reactants are m1_m2:FC(C=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)Cl)(F)F, amount is: 0.0 ;m1_m2:NCCCO, 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(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)NCCCO)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 50 mg (0.143 mmol) of N-(3-trifluoromethyl-phenyl)-4-(2-chloro4-pyridyl)-2-pyrimidineamine are stirred for 44 h at 100° in 1 ml of 3-amino-1-propanol. Concentration by evaporation and chromatography (methylene chloride:methanol=9:1) give N-(3-trifluoromethyl-phenyl)-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine; Rf =0.1 (methylene chloride:methanol=95:5), FAB-MS: 390, m.p. 158°-163°. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:C(C)(=O)C1=CC=[N+](C=C1)[O-], amount is: 0.0 ;m1_m2_m4:P(=O)(Cl)(Cl)Cl, amount is: 0.0 ;m3:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)C1=CC(=NC=C1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5.0 g (36.5 mmol) of 4-acetyl-pyridine N-oxide and 6.64 ml (73 mmol) of phosphorus oxychloride are stirred in 50 ml of toluene for 2 h at 100°. The reaction mixture is stirred at 50° into 500 ml of 10N sodium hydroxide solution, extracted with ethyl acetate and treated with Tonsil (Fluka; bentonite--colloidal aqueous aluminium silicate). Concentration and crystallisation (diethyl ether/n-hexane) give 4-acetyl-2-chloro-pyridine; |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(=O)C1=CC=NC=C1, amount is: 0.0 ;m1_m2_m3:ClC1=CC(=CC=C1)C(=O)OO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)C1=CC=[N+](C=C1)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The 4-acetyl-pyridine N-oxide used is prepared in the following manner: 11.0 ml (100 mmol) of 4-acetyl-pyridine and 31.3 g (100 mmol) of 55% m-chloro-perbenzoic acid are boiled under RF for 16 h in 200 ml of methylene chloride. Precipitation with 200 ml of diethyl ether gives 4-acetyl-pyridine N-oxide; m.p. 132°-133°. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)(=O)C1=CC(=NC=C1)Cl, amount is: 0.0 ;m1_m2:C(C)OC(N(C)C)OCC, 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:CN(C=CC(=O)C1=CC(=NC=C1)Cl)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 16.2 g (104.2 mmol) of 4-acetyl-2-chloro-pyridine are stirred at 110° with 116 ml of dimethylformamide diethylacetal for 1 h. Cooling to 0°, filtering and drying at 60° under HV give 3-dimethylamino-1-(2-chloro-4-pyridyl)-2-propen-1-one; 1H-NMR (dimethyl sulfoxide): 2.98 (3H,s), 3.2 (3H,s), 5.9 (1H,d), 7.8 (3H,m), 8.5 (1H |
Here is a chemical reaction formula: Reactants are m1_m2_m4:N#CN, amount is: 0.0 ;m1_m2_m4:FC(C=1C=C(N)C=CC1)(F)F, amount is: 0.0 ;m3:[N+](=O)(O)[O-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)(O)[O-].FC(C=1C=C(C=CC1)NC(=N)N)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 6.3 g (150 mmol) of cyanamide (50% in water) are added to a suspension of 16.1 g (100 mmol) of 3-trifluoromethyl-aniline in 35 ml of ethanol. 7.0 ml of nitric acid (65%, 0.1 mol) are then added to the brown solution and the reaction mixture is heated for 20 h under RF. It is then cooled to 0° and filtered, and the material retained on the filter is washed with ethanol and dried at 60° under HV to give 3-trifluoromethyl-phenylguanidine nitrate; 1H-NMR (dimethyl sulfoxide): 7.6 (7H,m), 9.9 (1H,br,s). |
Here is a chemical reaction formula: Reactants are m1:CN(C=CC(=O)C1=CC(=NC=C1)Cl)C, amount is: 0.0 ;m2_m3:[N+](=O)(O)[O-].FC(C=1C=C(C=CC1)NC(=N)N)(F)F, amount is: 0.0 ;m2_m3:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CC(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(C=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)Cl)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 150 mg (0.71 mmol) of 3-dimethylamino-1-(2-chloro-4-pyridyl)-2-propen-1-one are suspended in 1.5 ml of 2-propanol. 190 mg (0.712 mmol) of 3-trifluoromethylphenyl-guanidine nitrate and 31 mg (0.783 mmol) of sodium hydroxide are added and the reaction mixture is stirred for 18 h under RF. It is then cooled to RT and filtered, and the material retained on the filter is washed with 2-propanol and water and dried at 50° under HV to give N-(3-trifluoromethyl-phenyl)-4-(2-chloro-4-pyridyl)-2-pyrimidineamine; |
Here is a chemical reaction formula: Reactants are m1_m3:ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC=[N+](C=C1)[O-], amount is: 0.0 ;m1_m3:P(=O)(Cl)(Cl)Cl, amount is: 0.0 ;m2:[OH-].[Na+], 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:ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 10.0 g (32 mmol) of N-(3-chloro-phenyl)-4-(N-oxido-4-pyridyl)-2-pyrimidineamine are stirred for 24 h in 100 ml of phosphorus oxychloride at 110°. The reaction mixture is stirred at 50° into 2N sodium hydroxide solution and extracted with tetrahydrofuran. Concentration and crystallisation (tetrahydrofuran/ethanol) of the residue give N-(3-chloro-phenyl)-4-(2-chloro4-pyridyl)-2-pyrimidineamine; m.p. 196°-198°, Rf =0.7 (methylene chloride:methanol=95:5). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC=NC=C1, amount is: 0.0 ;m1_m2_m3:ClC1=CC(=CC=C1)C(=O)OO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC=[N+](C=C1)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 10 g (35.4 mmol) of N-(3-chloro-phenyl)-4-(4-pyridyl)-2-pyrimidineamine and 11.1 g (35.4 mmol) of m-chloroperbenzoic acid are stirred for 5 h at RT in 500 ml of methylene chloride. Concentration and crystallisation (acetic acid) of the residue give N-(3-chloro-phenyl)-4-(N-oxido4-pyridyl)-2-pyrimidineamine; m.p. 274°-275°, Rf =0.6 (methylene chloride:methanol=9:1). |
Here is a chemical reaction formula: Reactants are m1_m2:ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)Cl, amount is: 0.0 ;m1_m2:C(CN)N, 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:ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)NCCN, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 20 mg (0.063 mmol) of N-(3-chloro-phenyl)-4-(2-chloro-4-pyridyl)-2-pyrimidineamine are stirred for 26 h at 110° with 1 ml of ethylenediamine. Concentration and chromatography (methylene chloride:methanol:conc. ammonia solution=80:20: 1) give N-(3-chloro-phenyl)-4-[2-(2-amino-ethyl-amino)-4-pyridyl]-2-pyrimidineamine; Rf =0.15 (methylene chloride:methanol:conc. ammonia solution=80:20:1), FAB-MS: 341 (M+ +1). |
Here is a chemical reaction formula: Reactants are m4_m6:C(CN)N, amount is: 0.0 ;m1_m2_m3_m5:ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)C(=O)O, amount is: 0.0 ;m1_m2_m3_m5:Cl.C(C)N=C=NCCCN(C)C, amount is: 0.0 ;m1_m2_m3_m5:ON1C(CCC1=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m6:CN(C)C=O, amount is: 0.0 ;m1_m2_m3_m5:CN(C=O)C, amount is: 0.0 ;m7:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)C(=O)NCCN, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 80 mg (0.24 mmol) of N-[3-chloro-phenyl]-4-(2-carboxy-4-pyridyl)-2-pyrimidineamine, 70.8 mg (0.36 mmol) of N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride and 42 mg (0.36 mmol) of N-hydroxysuccinimide are dissolved in 3 ml of dimethylformamide and stirred for 2.5 h at RT. The reaction mixture is then added dropwise at 0° within a period of 30 minutes to a solution of 0.77 ml (11.8 mmol) of ethylenediamine in 2 ml of DMF. After stirring for 14 h at RT, the reaction mixture is poured into 50 ml of ethyl acetate and extracted with 30 ml of water. The organic phase is dried (sodium sulfate) and concentrated. Crystallisation from isopropanol/ethanolic hydrochloric acid gives N-[3-chloro-phenyl]-4-[2-(N-{2-amino-ethyl}-aminocarbonyl)-4-pyridyl]-2-pyrimidineamine hydrochloride; m.p. 161°-163°, FAB-MS: 369 (M+ +H). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(=O)(O)C=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)NCCCO, amount is: 0.0 ;m1_m2_m3:S(O)(O)(=O)=O, amount is: 0.0 ;m1_m2_m3:CO, 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:COC(=O)C=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)NCCCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2.0 g (5.4 mmol) of N-[3-carboxy-phenyl]-4-(2-(3-hydroxy-propyl-amino)-4-pyridyl)-2-pyrimidineamine and 0.28 ml (5.4 mmol) of conc. sulfuric acid are boiled under RF in 150 ml of methanol for 24 h. After cooling to RT, the reaction mixture is concentrated to half the volume, diluted with 100 ml of ethyl acetate and extracted twice with 50 ml of buffer (pH 7) each time. The organic phase is dried (Na2SO4) and concentrated. Crystallisation (methylene chloride/methanol) gives N-[3-methoxycarbonylphenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine; m.p. 162°-163°, FAB-MS: 380 (M+ +H). |
Here is a chemical reaction formula: Reactants are m1_m2:COC(=O)C=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)NCCCO, amount is: 0.0 ;m1_m2:NCCCN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NCCCNC(=O)C=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)NCCCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 100 mg (0.26 mmol) of N-[3-methoxycarbonyl-phenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine and 0.5 ml of 1,3-diamino-propane are stirred for 24 h at 90° and then diluted with 20 ml of ethyl acetate and extracted with 2×10 ml of sodium chloride solution. The organic phase is dried, concentrated and crystallised from methylene chloride/diethyl ether to give N-[3-{N-(3-amino-propyl)-aminocarbonyl}-phenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine; |
Here is a chemical reaction formula: Reactants are m0_m1_m2_m4_m3:C(Cl)Cl, amount is: 0.0 MOLE;m0_m1_m2_m4_m3:ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)N1CCNCC1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m0_m1_m2_m4_m3:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)Cl;0:N1CCNCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Analogously to Example 1, there is obtained from 100 mg (0.31 mmol) of N-[3-chloro-phenyl]-4-(2-chloro-4-pyridyl)-2-pyrimidineamine and 500 mg (5.63 mmol) of piperazine, from the melt after chromatography (methylene chloride:methanol=95:5), N-[3-chloro-phenyl]-4-[2-(1-piperazinyl)-4-pyridyl]-2-pyrimidineamine; |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=CC=C(C(=O)CCC(=O)O)C=C1, amount is: 0.0 ;m1_m3_m2:O.NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1CCC(NN1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-(4-chlorobenzoyl)propionic acid (20 g) in absolute ethanol (200 ml) was added 5 g of hydrazine monohydrate. A thick solid was formed which dissolved after heating. The resulting solution was refluxed for 3 h, cooled and the solid formed filtered and dried to yield 16 g (80%) of 6-(4-chlorophenyl)-4,5-dihydropyridazinone. |
Here is a chemical reaction formula: Reactants are m2:O1CCCC=C1, amount is: 0.0 ;m1_m3_m5:C(C#CCO)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m5:CCOCC, amount is: 0.0 ;m4:CCOCC, amount is: 0.0 MOLE,Catalysts are m1_m3_m5:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 .Products are 0:O1C(CCCC1)OCC#CCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic acid and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC1=CC=C(C=C1)C=1CCC(NN1)=O, amount is: 0.0 ;m1_m2_m3:C(C)(=O)O, amount is: 0.0 ;m1_m2_m3:BrBr, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1C=CC(NN1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 6-(4-chlorophenyl)-4,5-dihydropyridazinone (11.75 g) and glacial acetic acid (100 ml) was added dropwise 3 ml of bromine and the mixture was heated at 60°-70° C. for 3 h. The resulting mixture was cooled and slowly poured into 400 ml of cold water. The resulting white solid was filtered and dried to yield 10.83 g (89%) of 6-(4-chlorophenyl)pyridazinone. |
Here is a chemical reaction formula: Reactants are m2_m3:O, amount is: 0.0 ;m2_m3:Cl, amount is: 0.0 ;m1_m4_m5:ClC1(C(C(C1)(F)F)(F)Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m5:CCOCC, amount is: 0.0 ;m1_m4_m5:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1(C(C=C1Cl)(F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1,1,2 trichloro-2,3,3-trifluorocyclobutane (55.5 g) in 100 ml of anhydrous ether, triethylamine (40 ml) was added dropwise over 30 min at room temperature, and the mixture was stirred overnight at ambient temperature. The mixture was then stirred with 120 ml H2O and 7.5 ml of concentrated HCl. The ether layer was washed with H2O (100 ml), brine (100 ml), dried over anhydrous MgSO4, and evaporated in vacuo. The residue was distilled fractionally at atmospheric pressure from 64°-68° C. to yield 36 g (79%) of a colorless liquid as pure product. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC(C(C(=O)O)(F)F)(C(=O)O)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:O1CCOCC1, amount is: 0.0 ,Catalysts are m1_m2_m3:[Zn], amount is: 0.0 .Products are 0:FC(C(=O)O)(C(C(=O)O)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirring solution of the chlorotrifluorosuccinic acid (part b) (24.5 g) in 200 ml dioxane was added portionwise zinc metal (85 g) and the mixture was stirred at ambient temperature for 10 hours to yield a viscous liquid which was decanted from the unreacted zinc. Most of the dioxane was evaporated in vacuo. The residue was dissolved in 100 ml H2O and a solution of 7.7 ml of concentrated H2SO4 in 25 ml of water was added. The solution was extracted with ether (3×100 ml) and dried over anhydrous MgSO4. The organic layer was stripped to yield 8.3 g (32%) of the product as a crystalline solid. |
Here is a chemical reaction formula: Reactants are m2:O, amount is: 0.0 MOLE;m1_m4_m3:C(C1=CC=CC=C1)(=O)CCCC(=O)O, amount is: 0.0 ;m1_m4_m3:NN, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:CCOCC, amount is: 0.0 ;m6:C1(=CC=CC=C1)C, amount is: 0.0 MOLE;m1_m4_m3:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)C1=CC=CC(N=N1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 10 g (0.052 mole) of 4-benzoylbutyric acid in 300 ml of toluene, hydrazine was added in one portion and the reaction was heated to reflux until all water had ceased to azeotrope. The reaction mixture was cooled and the toluene was stripped off in vacuo. The residue was dissolved in 200 ml Et2O and washed with H2O (100 ml) and brine (100 ml). The ether extract was dried over anhydrous MgSO4, filtered and stripped to yield an orange semisolid which was triturated with ether to yield 3.8 g (39%) of the desired product as a yellow solid. |
Here is a chemical reaction formula: Reactants are m4:COC(OC)=O, amount is: 0.0 ;m1_m6_m2_m5:[H-].[Na+], amount is: 0.0 ;m1_m6_m2_m5:ClC=1C=C2CCC(C2=CC1)=O, amount is: 0.0 ;m3:[H][H], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m6_m2_m5:C(OC)COC, amount is: 0.0 ;m1_m6_m2_m5:C(OC)COC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of sodium hydride (2.4 g, 60% in mineral oil, 0.06. mole) and 50 ml dry dimethoxyethane, 5-chloroindanone (50 g, 0.03 mole) in 50 ml dimethoxyethane was added dropwise at room temperature. The mixture was stirred at room temperature until hydrogen evolution ceased. Then dimethylcarbonate (27 g, 0.3 mole) was added dropwise at room temperature and the reaction was heated to 60° C. for one hour. The reaction was cooled to room temperature, quenched with 100 ml H2O, acidified to pH 5 with concentrated HCl and extracted with ethyl ether (3×100 ml). The ether extract was washed with brine (100 ml), dried over anhydrous MgSO4 and stripped to yield 3.0 g (45%) of the desired product as a tan solid. |
Here is a chemical reaction formula: Reactants are m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 MOLE;m2:CN(C)C=O, amount is: 0.0 ;m3:ClC1=CC=C(C=C1)CC(=O)O, amount is: 0.0 ;m1:P(=O)(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C(C=O)=CN(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phosphorus oxychloride (92 g) was added dropwise to stirred DMF (78 ml) between 10°-15° C. To the resulting slurry was added 4-chlorophenylacetic acid (34.12 g). The resulting mixture was stirred at room temperature for one half hour and then heated to 70°-80° C. during 5.5 hours, during which time the mixture became effervescent. The reaction mixture was cooled and poured slowly onto cracked ice. The resulting suspension was brought to pH 10 with solid potassium carbonate. Ice was added intermittently during this addition to maintain the temperature below 15° C. Toluene (150 ml) was added and the resulting mixture heated at 100° C. for one hour. The mixture was cooled and allowed to stand overnight. The two resulting layers were separated and the aqueous layer extracted with toluene (2×100 ml). The combined organic layers were washed with water (5×200 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo and the resulting yellow solid was triturated with hexane to yield 26 g of 2-(4-chlorophenyl)-3-dimethylaminopropenal as a tan solid mp. 120°-125° C. |
Here is a chemical reaction formula: Reactants are m1_m5_m2:C[O-].[Na+], amount is: 0.0 ;m1_m5_m2:C(#N)CC(=O)N, amount is: 0.0 ;m3:ClC1=CC=C(C=C1)C(C=O)=CN(C)C, amount is: 0.0 MOLE;m4:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:CO, amount is: 0.0 ;m6:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To solution of sodium methoxide (7.52 g) in methanol (130 ml) was added cyanoacetamide (5.84 g) followed by 2-(4-chlorophenyl)-3-dimethylaminopropenal and the resulting suspension was refluxed overnight. During this time a yellow solid was formed. The mixture was cooled to room temperature and glacial acetic acid (50 ml) was added followed by water (100 ml). The resulting yellow orange solid was filtered off, washed several times with water and dried to yield 8.1 g of 3-cyano-5-(4-chlorophenyl)-2-pyridinone. |