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Here is a chemical reaction formula: Reactants are m3:CN, amount is: 0.0 MOLE;m1_m2_m5:CN, amount is: 0.0 MOLE;m1_m2_m5:C(C1=CC=CC=C1)=O, amount is: 0.0 ;m4:CN, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m5:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)=CN, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Anhydrous monomethylamine (about 1-1.5 eq,) was introduced below the surface of a stirred solution of benzaldehyde (1062 g, 10.0 mol) in toluene (2000 ml) cooled to 0° C. The rate of addition of monomethylamine was adjusted so as to maintain the reaction temperature between 25°-30° C.; after 45 minutes the addition of monomethylamine was terminated. The organic phase was separated and concentrated in vacuo. Distillation of the residual oil afforded N-benzylidenemethylamine (1047g, 8.79 mol) in 88% yield. The product had a boiling point of 79° C. at 20 mm. [This N-benzylidinemethylamine starting material is reported by R. B. Moffett et al, Org. Syn. Coll. Vol. IV, 605-608 (1963)]. |
Here is a chemical reaction formula: Reactants are m1_m3:Cl.Cl.CNC(CC1=C(C=CC=C1)N)C1=CC=CC=C1, amount is: 0.5 MOLE;m2:C(C)C(C([O-])([O-])[O-])(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CNC(CC1=C(C=CC=C1)NC(C(C)(C)C)=O)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A heterogeneous mixture of N-methyl-2-amino-α-phenylphen-ethylamine dihydrochloride (150g, 0.5 mol) in acetonitrile (500 ml) was treated with triethylorthoacetate (202 ml, 1.1 mol) and heated to 70° C. for 2 hours with stirring under a dry nitrogen atmosphere. The reaction mixture was filtered, concentrated in vacuo, and the residual solid recrystallized from 2-propanol at -10° C. to give 2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine hydrochloride (118g, 0.413 mol) in 83% yield. The product had a melting point of 239.5°-241° C. |
Here is a chemical reaction formula: Reactants are m1_m2:ClC=1C=NC2=C(C(=CC=C2C1)Cl)C(=O)O, amount is: 0.0 ;m1_m2:S(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC=1C=NC2=C(C(=CC=C2C1)Cl)C(=O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3,7-Dichloro-8-quinolinecarboxylic acid(20 g, 82 mmol) was added to thionyl chloride(80 ml), and the mixture refluxed for 3 hours and concentrated under reduced pressure to afford the desired product(20.6 g, yield=95.7%) as a light brown solid. |
Here is a chemical reaction formula: Reactants are m3_m4_m6:CCC(=O)N(C=1C=CC=CC1)C2(CCN(CC2)CCC3=CC=CS3)COC, amount is: 0.0 MOLE;m3_m4_m6:C(CC(O)(C(=O)O)CC(=O)O)(=O)O, amount is: 0.0 MOLE;m1:CCC(=O)N(C=1C=CC=CC1)C2(CCN(CC2)CCC3=CC=CS3)COC.Cl, amount is: 0.0 MOLE;m2:[OH-].[K+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE;m3_m4_m6:C(C)O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CCC(=O)N(C=1C=CC=CC1)C2(CCN(CC2)CCC3=CC=CS3)COC.C(C(=O)O)C(CC(=O)O)(C(=O)O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sufentanil HCl obtained in Example 8 was suspended in hot water and adjusted to pH 10-11 with 10% aqueous potassium hydroxide and extracted with ether. The organic layer washed with water, dried and evaporated to give the free base with an LC purity profile of 99.62%. An equivalent of sufentanil free base with anhydrous citric acid was warmed in 100% ethanol. After removal of ethanol the fluffy white powder was dried in the vacuum oven at 56° C. for 48 hrs. Sufentanil citrate thus obtained passed all USP tests. |
Here is a chemical reaction formula: Reactants are m1:C([O-])([O-])=O.[Na+].[Na+], amount is: 0.0 ;m2:Cl.COC(=O)[C@@H]1NC[C@H](CC1)C(=O)OC, amount is: 0.0 ;m3_m6:O(S(=O)(=O)C(F)(F)F)CCN1C(C=2C(C1=O)=CC=CC2)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 ;m5:C(Cl)Cl, amount is: 0.0 ;m3_m6:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(C=2C(C(N1CCN1[C@H](CC[C@@H](C1)C(=O)OC)C(=O)OC)=O)=CC=CC2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a well-stirred bi-phasic mixture consisting of sodium carbonate (500 g, 4.72 mol) in water (3 liters) and trans-2,5-piperidine dicarboxylate dimethyl ester hydrochloride (280 g, 1.18 mol) in methylene chloride (4.5 liters), a solution of 2-phthalimido-ethyl triflate (417 g, 1.29 mol) in methylene chloride (3 liters) was added in a steady stream over a 3 hour period. The organic layer was separated, and the aqueous layer was extracted with fresh methylene chloride (3 liters). The combined organic extracts were washed with water (3 liters), then with brine (3 liters), dried with anhydrous magnesium sulfate and finally, concentrated in vacuo to a solid. The entire residue was triturated in refluxing ether (3 liters), with vigorous stirring, for 15 minutes. After cooling to ambient temperature, the solution was poured into hexanes (3 liters), and the resulting mixture was stirred for 18 hours. The resulting colorless solid was collected by filtration, and the filter cake was washed with hexanes (1 liter). In vacuo drying afforded 437.3 g (99.1% yield) of the title compound as a colorless solid. TLC Rf (ethyl acetate/methylene chloride =1:1 in volume; iodoplatinate spray): 0.5. |
Here is a chemical reaction formula: Reactants are m3_m5:CC(C)C[AlH]CC(C)C, amount is: 0.0 MOLE;m1_m2_m4:C(#N)[C@H]1C[C@@H](O[C@@H]1COC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)N1C(=O)NC(=O)C=C1, amount is: 0.0 ;m1_m2_m4:[C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C(C)=C1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m5:C1(=CC=CC=C1)C, amount is: 0.0 ;m1_m2_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C=C1)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 3'- cyano-2', 3'-dideoxy-5'-O-trityluridine (0.96 g, 2 mmol), (prepared in a manner equivalent to that of the thymidine analog above) in dry THF (20 ml) under argon, was added a solution of DIBAL-H in toluene (Aldrich) (1M, 4 ml) at -10° C. over a period of 10 min. After 36 mins the reaction was quenched with MeOH (5 ml) at -10° C. The mixture was further stirred at ambient temperature for 30 mins and diluted with CH2Cl2 (25 ml) before concentrating under vacuum. This process was repeated with CH2C2 (3×25 ml) in order to remove the residual THF. The residue was purified by flash chromatography on silica gel (25 g). Elution with CH2Cl2 (9:1, v/v) and crystallization from CH2Cl2 /MeOH gave 5'-O-trityl-3'-C-formyl-2',3'-dideoxyuridine (0.53 g, 53%); mp 100° C.; 1H NMR (CDCl3) δ2.25-2.8 (m, 2, CH2), 3.4 (m, 1, C3'H), 3.45-3.6 (m, 2, C5'CH2), 4.37 (m, 1, C4, H), 5.4 (d, 1, C5H), 6.1 (m, 1, C1', H), 7.2-7.4 (m, 15, C6H5), 7.81 (d, 1, C6H), 7.95 (br s, 1, NH), 9.61 (s, 1, HC=O). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)O[C@H]1C[C@@H](O[C@@H]1CON1C(C=2C(C1=O)=CC=CC2)=O)N2C(=O)NC(=O)C(C)=C2, amount is: 0.0 ;m1_m3_m2:CNN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NOC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 3'-O-(t-butyldiphenylsilyl)-5'-O-phthalimidothymidine (10 g, 16 mmol) in dry CH2Cl2 (100 ml) was added methylhydrazine (1.3 ml, 24 mmol) under argon at room temperature and solution stirred for 12 h. The solution was cooled (0° C.) and filtered. The white residue was washed with CH2Cl2 (2×25 ml) and combined filtrates were evaporated to furnish gummy residue. The residue on purification by silica gel column chromatography (elution with CH2Cl2 :MeOH, 98:2, v/v) furnished 7.03 g (89%) of 5'-O-amino-3'-O-(t-butyldiphenylsilyl)thymidine that crystallized from CH2Cl2 /MeOH mp 141°-143° C. 1H NMR (DMSO-d6) δ11.29 (s, 1, NH), 7.42-7.62 (m, 11, TBDPhH, C6H), 6.25 (dd, 1, H1', J1',2' =8.4 Hz, J1',2" =6.3 Hz), 6.02 (s, 2, NH2), 4.35 (m, 1, H4'), 4.04 (m, 1, H3'), 3.34-3.51 (m, 2, H5',5"), 2.04 (m, 2, H2', 2"), 1.73 (s, 3, CH3), 1.03 (s, 9, C(CH3)3). Anal. Calcd. for C26H33O5N3Si: C, 63.00; H, 6.71; N, 8.48. Found: C, 62.85; H, 6.67; N, 8.32. |
Here is a chemical reaction formula: Reactants are m4:CC(C)OC(=O)/N=N/C(=O)OC(C)C, amount is: 0.0 ;m5_m2_m3:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m5_m2_m3:ON1C(C=2C(C1=O)=CC=CC2)=O, amount is: 0.0 ;m1:[Si](C)(C)(C(C)(C)C)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5_m2_m3:C1CCOC1, amount is: 0.0 ;m6_m7_m9_m8_m0:CCOCC, amount is: 0.0 MOLE;m6_m7_m9_m8_m0:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)ON1C(C=2C(C1=O)=CC=CC2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 5'-O-t-butyldimethylsilylthymidine [1, 21.36 g, 60 mmol, prepared according to the procedure of Nair, et al., Org. Prep. Procedures Int. 1990, 22, 57 in dry THF (750 ml)], triphenylphosphine (17.28 g, 66 mmol) and N-hydroxyphthalimide (10.74 g, 66 mmol) were added. The solution was cooled to 0° C. and diisopropylazodicarboxylate (15.15 g, 75 mmol) was added dropwise over a period of 3 hr while stirring under nitrogen. The reaction mixture was then stirred at room temperature for 12 hr. The solution was evaporated and the residue was dissolved in CH2Cl2 (750 ml), extracted with sat. NaHCO3 (200 ml), and water (200 ml), dried (MgSO4), filtered and concentrated to furnish yellow oily residue. Silica gel column chromatography (100% hexanes, and then hexanes:Et2O gradient to 90% Et2O) of the residue gave compound 2 as a colorless glass (18.68 g, 62%); 1H NMR (CDCl3) δ0.05 [2s, 6, (CH3)2 ], 0.91 [s, 9, (CH3)3 ], 2.0 (s, 3, CH3), 2.5-2.65 (m, 2, 2'CH2), 4.05-4.2 (m, 2, 5'CH2), 4.25-4.35 (m, 1, 4'H), 5.0 (m, 1, 3'H) 6.15 (m, 1, 1'H), 8.6 (br s, 1, NH), and aromatic protons. Anal. Calcd. for C24H31N3O7Si: C, 57.46;H, 6.23; N, 8.37. found: C, 57.20; H, 6.26; N, 8.27. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:CNN, amount is: 0.0 ;m1_m2_m3:[Si](C)(C)(C(C)(C)C)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)ON1C(C=2C(C1=O)=CC=CC2)=O, 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:NO[C@H]1C[C@@H](O[C@@H]1CO[Si](C)(C)C(C)(C)C)N1C(=O)NC(=O)C(C)=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Cold methylhydrazine (1.6 ml, 30 mmol) was added to a stirred solution of 5'-O-(t-butyldimethylsilyl)-3'-O-phthalimidothymidine (2, 4.6 g, 9.18 mmol) in dry CH2Cl2 (60 ml) at 5°-10° C. After 10 minutes white precipitation of 1,2-dihydro-4-hydroxy-2-methyl-1-oxophthalizine occurred. The suspension was stirred at room temperature for 1 h. The suspension was filtered and precipitate washed with CH2Cl2 (2×20 ml). The combined filtrates were concentrated and the residue purified by silica gel column chromatography. Elution with CH2Cl2 :MeOH (100:0→97:3, v/v) furnished the title compound (3.40 g, 100%) as white solid. Crystallization from CH2Cl2 gave white needles, m.p. 171° C.; 1H NMR (CDCl3) δ0.05 [s, 6, (CH3)2 ], 0.90 [s, 9, (CH3)3 ], 2.22-2.58 (2 m, 2, 2'CH2), 3.9-4.08 (m, 3, 5'CH2, and 3'H) 4.30 (m, 1, 4'H) 5.5 (br s, 2, NH2) 6.2 (m, 1, 1'H) 7.45 (s, 1, C6H) 8.9 (br s, 1, NH). Anal. Calcd. for C16H29N3O5Si: C, 51.72; H, 7.87; N, 11.32. found: C, 51.87, H, 7.81; N, 11.32. |
Here is a chemical reaction formula: Reactants are m2:[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].C1CCOC1, amount is: 0.0 MOLE;m1:NO[C@H]1C[C@@](O[C@@H]1CO)(N1C(=O)NC(=O)C(C)=C1)[Si](C)(C)C(C)(C)C, 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:NO[C@H]1C[C@@H](O[C@@H]1CO)N1C(=O)NC(=O)C(C)=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3'-O-Amino-(t-butyldimethylsilyl)thymidine was deblocked with (Bu)4NF/THF in standard way to furnish compound 4 (72%). Crystallized from ether/hexanes/ethanol as fine needles, mp 81° C. 1H NMR (Me2SO-d6) δ1.78 (s, 3, CH3), 2.17 and 2.45 (2 m, 2, 2'CH2), 3.70 (m, 2, 5'CH2), 3.88 (m, 1, 4'H), 4.16 (m, 1, 3'H), 4.8 (br s, 1, 5'OH), 6.05 (dd, 1, 1H), 6.2 (br s, 2 NH2), 7.48 (s, 1, C6H), and 11.24 (br s, 1, NH). Anal. Calcd. for C10H15N3O5 : C, 46.69; H, 5.87; N, 16.33; found: C, 46.55; H, 5.91; N, 16.21. |
Here is a chemical reaction formula: Reactants are m3:C=O, amount is: 0.0 ;m1_m2_m4:C=O, amount is: 0.0 ;m1_m2_m4:NO[C@H]1C[C@@H](O[C@@H]1CO[Si](C)(C)C(C)(C)C)N1C(=O)NC(=O)C(C)=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)ON=C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of HCHO (20% aqueous, 1 ml) was added dropwise to a stirred solution of 3'-O-amino-5'-O-(t-butyldimethylsilyl)thymidine (3, 7.42 g, 20 mmol) in dry MeOH (400 ml) at room temperature. After 6 h, another portion of HCHO (20% aqueous, 1.5 ml) was added and stirring continued for 16 h. The resulting solution was evaporated under reduced pressure, and the residue was purified by chromatography on silica gel to give compound 10 (7.25 g, 95%) as clear foam. 1H NMR (CDCl3) δ0.1 [s, 3, (CH3)2 ], 0.9 [s, 9, (CH3)3 ], 1.9 (s, 3, CH3), 2.25-2.72 (m, 2, 2' CH2), 3.85-4.15 (2m, 3, 5' CH2, 4' H), 4.85 (m, 1, 3'H), 6.25 (dd, 1, 1'H) 6.5 and 6.95 (2d, 2, N=CH2), 7.43 (s, 1, (6H), 9.2 (br s, 1 NH). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:O=CC1=C(O)C(OC)=CC=C1, amount is: 0.0 ;m1_m2_m3_m4:C(C1=CC=CC=C1)Br, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:COC=1C(=C(C=O)C=CC1)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 196.0 g (1.30 mole) of o-vanillin (Aldrich), 200 g of benzyl bromide (Aldrich), 500 g of anhydrous potassium carbonate and 1,500 mL of absolute ethanol is heated, with stirring, at reflux for 6 hours. After cooling, the supernatant is decanted and the remainder is filtered. The combined filtrate and supernatant is concentrated at reduced pressure to remove solvent. The remaining oil is extracted into 1 L of ether. The ether solution is washed with 500 mL of water, 600 mL of 1% potassium hydroxide solution, and 500 mL of water and then dried (potassium carbonate) and concentrated to give 263.4 g (84% yield) of product; mp 41-43° C. Reported mp, 43° C. (Chem. Abstr. 62: 16110a). |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 ;m3:C(C1=CC=CC=C1)=C1C(NC(N1)=O)=O, amount is: 0.0 MOLE;m6_m1_m5:COC=1C(=C(C=CC1)C=C1C(NC(N1)=O)=O)OCC1=CC=CC=C1, amount is: 0.0 ;m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6_m1_m5:CO, amount is: 0.0 MOLE,Catalysts are m6_m1_m5:[Zn], amount is: 0.0 .Products are 0:COC=1C(=C(C=CC1)CC1C(NC(N1)=O)=O)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Zinc powder (40.00 g; 0.61 mole) is added to a stirred suspension of 48.00 g (0.16 mole) of the benzylidine hydantoin from Example 3 in 1,200 mL of methanol under nitrogen. Concentrated hydrochloric acid (30 mL) is added and the mixture is heated on the steam bath for 20 minutes (after 10 minutes the starting benzylidene hydantoin dissolves). Another 30 mL of concentrated hydrochloric acid is added and the mixture is heated at reflux for another 20 minutes. The cooled (50° C.)mixture is cautiously filtered and the cake washed with 100 mL of methanol. Water (500 mL) is added to the filtrate to yield 24.60 g of crystalline product; mp 202°-204° C. Recrystallization from methanol gives pure product; mp 205°-207° C. |
Here is a chemical reaction formula: Reactants are m1:C1(=CC=CC=C1)C(C(=O)N1CC2=CC=C(C(=C2CC1C(=O)OC)OC1=CC=C(C=C1)[N+](=O)[O-])OC)C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2:CO.C1CCOC1, amount is: 0.0 MOLE,Catalysts are m3:[Pd], amount is: 0.0 MOLE.Products are 0:NC1=CC=C(OC2=C3CC(N(CC3=CC=C2OC)C(C(C2=CC=CC=C2)C2=CC=CC=C2)=O)C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 0.80 g (1.45 mmole) of the nitrobenzene derivative of Example 43 in 50% methanol-THF is reduced with 5% palladium-on-carbon catalyst. The filtered solution is concentrated at reduced pressure to give 0.75 g of pure product as a solid foam; mass spectrum (EI) 522 (M+). |
Here is a chemical reaction formula: Reactants are m1:C1(CCCCC1)=O, amount is: 0.0 ;m2_m3:C(C)(C)(C)OOC(C)(C)C, amount is: 0.0 ;m2_m3: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:C(C)OCCC1C(CCCC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2940 g (30 mol) of cyclohexanone were heated to reflux while stirring and, at this temperature, a solution of 87.6 g (0.6 mol) of di-tert-butyl peroxide in 216 g (3 mol) of ethyl vinyl ether was added over the course of 5 hours (h). The mixture was subsequently refluxed for a further 1 h. After the mixture had cooled, the low boilers (tert-butanol, remaining vinyl ether and peroxide) and the excess cyclohexanone were removed by distillation under reduced pressure (25-40 mbar; diaphragm pump). The residue (about 500 g) was distilled under reduced pressure (0.5 to 2 mbar; oil pump). A total of 350 g of a 95% pure 2-(2-ethoxyethyl)cyclohexanone of boiling point 60°-65° C. (0.5 mbar) was obtained, corresponding to a yield of 69% of theory. |
Here is a chemical reaction formula: Reactants are m2_m3_m4:OC1COC1, amount is: 0.0 ;m2_m3_m4:N1=CC=CC=C1, amount is: 0.0 ;m1_m5:C(C)(C)C1=C(C(=S)Cl)C=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3_m4:C1(=CC=CC=C1)C, amount is: 0.0 ;m1_m5:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)C1=C(C(=S)OC2COC2)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 12.9 g of 2-isopropylthiobenzoyl chloride and 20 ml of absolute toluene is added dropwise to a mixture of 4.44 g of 3-hydroxyoxetane, 6.64 g of pyridine and 60 ml of absolute toluene at a temperature of 15°to 20° C. The suspension formed is stirred at a temperature of 20°-25° C. for 2 hours and at a temperature of 40°-45° C. for a further 3 hours. Adding water to the reaction mixture, washing the organic phase with water and drying and evaporating it gives 12.6 g of oxetan-3-yl 2-isopropylthiobenzoate as a pale yellow oil. |
Here is a chemical reaction formula: Reactants are m4:S(O)(O)(=O)=O, amount is: 0.0 MOLE;m1:O1CC=CC2=CC=CC=C12, amount is: 0.0 MOLE;m2_m3:C(CCC)(=O)CC(=O)OCC, amount is: 0.0 MOLE;m2_m3:C1(O)=CC(O)=CC(O)=C1, amount is: 0.0 MOLE;m5_m6_m7:C(CC)(=O)Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5_m6_m7:C(=S)=S, amount is: 0.0 MOLE;m5_m6_m7:[N+](=O)([O-])C1=CC=CC=C1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:OC1=C2C(=CC(OC2=C(C(=C1)O)C(CC)=O)=O)CCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The key intermediate in the inventive method of preparation is chromene 4, which is synthesized by the sequence depicted in Scheme I. Thus, 5,7-dihydroxy-4-propylcoumafin, 2,5 was prepared quantitatively from ethyl butyrylacetate and phloroglucinol under Pechman conditions.6Product yield and purity was dependent on the amount of sulfuric acid used. The 8-position of 5,7-dihydroxy-4-propylcoumafin, 2, was then selectively acylated at 8°-10° C. by propionyl chloride and A1Cl3 in a mixture of carbon disulfide and nitrobenzene to afford 5,7-dihydroxy-8-propionyl-4-propylcoumarin, 3. A route developed for synthesis of Mammea coumarins7 was initially attempted for preparation of compound 3, but it proved too awkward and low-yielding. The chromene ring was introduced upon treatment of compound 3 with 4,4-dimethoxy-2-methylbutan-2-ol,8 providing 4 in 78% yield. ##STR2## |
Here is a chemical reaction formula: Reactants are m1_m2:OC1=C2C(=CC(OC2=C(C(=C1)O)C(CC)=O)=O)CCC, amount is: 0.0 ;m1_m2:COC(CC(C)(O)C)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC1=C(C=2OC(C=C(C2C=2OC(C=CC21)(C)C)CCC)=O)C(CC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3 (2.60 g, 9.42 mmol) and 4,4-dimethoxy-2-methylbutan-2-ol (5.54 g, 37.7 retool) were dissolved in anhydrous pyridine (6.5 mL). The mixture was refluxed under nitrogen for three days. After removal of the solvent in vacuo, the residue was dissolved in ethyl acetate. The ethyl acetate was washed several times with 1N HCl and brine. It was then dried over Na2SO4. The crude product obtained by evaporation in vacuo was purified by silica gel column chromatography, eluting with 25% ethyl acetate/hexane to afford 2.55 g of 4 in 78.6% yield, mp 96°-98° C. 1H-NMR (CDCl3) δ 1.05 (3H, t, J =7.3 Hz, CH3); 1.22 (3H, t, J=7.5 Hz, CH3); 1.53 (6H, s, 2 CH3); 1.75 (2H, m, CH2); 2.92 (2H, t, J=7.1 Hz, CH2); 3.35 (2H, q, J=7.1 Hz, CH2); 5.56 (1H, d, J=10.0 Hz, H3); 5.98 (1H, s, H9); 6.72 (1H, d, J=10.0 Hz, H4); MS (EI): 343 (5.7, M+1); 342 (22.5, M+); 327 (100, M-CH3); IR (KBr): 1728 (vs, C=O) cm-1 ; Anal. calc. for C20H22O5 : 70.16; H, 6.48; Found: C, 70.45; H, 6.92. |
Here is a chemical reaction formula: Reactants are m1_m2:C(CCC)(=O)CC(=O)OCC, amount is: 0.0 MOLE;m1_m2:C1(O)=CC(O)=CC(O)=C1, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:OC1=C2C(=CC(OC2=CC(=C1)O)=O)CCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: condensing ethyl butyrylacetate and phloroglucinol in the presence of an acid catalyst to form 5,7-dihydroxy-4-propylcoumarin; |
Here is a chemical reaction formula: Reactants are m1:OC1=C2C(=CC(OC2=CC(=C1)O)=O)CCC, amount is: 0.0 MOLE;m2:C(CC)(=O)Cl, 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(CC)C1=CC(OC2=C(C(=CC(=C12)O)O)C(CC)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: acylating 5,7-dihydroxy-4-propylcoumarin with propionyl chloride in the presence of a Lewis acid to form 4-propyl-5,7-dihydroxy-8-propionylcoumarin; |
Here is a chemical reaction formula: Reactants are m1:OC1=C2C(=CC(OC2=C(C(=C1)O)C(CC)=O)=O)CCC, amount is: 0.0 MOLE;m2:COC(CC(C)(O)C)OC, 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:OC1=C(C=2OC(C=C(C2C=2OC(C=CC21)(C)C)CCC)=O)C(CC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: reacting 5,7-dihydroxy-8-propionyl-4-propylcoumarin with 4,4-dimethoxy-2-methylbutan-2-ol so as to produce 5-Hydroxy-2,2-dimethyl-6-propionyl-10-propyl -2H,8H-benzo[1,2-b: 3,4-b']-dipyran-8one; |
Here is a chemical reaction formula: Reactants are m4_m5_m6_m7:BrCC1(COC1)CO, amount is: 0.0 MOLE;m4_m5_m6_m7:[N-]=[N+]=[N-].[Na+], amount is: 0.0 MOLE;m2:O1CCC1, amount is: 0.0 MOLE;m3:BrCC1(COC1)CO, amount is: 0.0 MOLE;m1:O1CCC1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4_m5_m6_m7:CC(=O)C, amount is: 0.0 MOLE;m4_m5_m6_m7:CN(C=O)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:N(=[N+]=[N-])CC1(COC1)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The oxetane of the present invention has the formula: ##STR1## The oxetane of Formula I, 3-azidomethyl-3-nitratomethyloxetane (ANMO), is synthesized using 3-bromomethyl-3-hydroxymethyl oxetane (BMHMO) as the starting material. Reaction of 3-bromomethyl-3-hydroxymethyloxetane with sodium azide (NAN3) in acetone or dimethylformamide (DMF) gives the corresponding 3-azidomethyl-3-hydroxymethyloxetane in essentially quantitative yield. Subsequent reaction of 3-azidomethyl-3-hydroxymethyloxetane with acetyl nitrate gives the oxetane AMNO. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:[N-]=[N+]=[N-].[Na+], amount is: 0.0 ;m1_m2_m3_m4:BrCC1(COC1)CO, amount is: 0.0 ;m1_m2_m3_m4:CC(=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N(=[N+]=[N-])CC1(COC1)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of sodium azide (9.5 g, 0.14 mol), 3-bromomethyl-3-hydroxymethyloxetane (24.0 g, 0.14 mol), 20 mL of acetone and 20 mL of water was refluxed for 12 h. The acetone was evaporated and the resulting residue was extracted with two portion of 40 mL of ethyl acetate. The combined organic extracts were dried over magnesium sulfate (MgSO4). The solvent was removed by evaporation. 18.0 g, representing a 94% yield, of 3-azidomethyl-3-hydroxymethyloxetane were obtained as an oil. This oil was found to be essentially pure by gas-liquid chromatography (GLC) analysis. NMR: 1H NMR 3.70 (s, 2H), 3.84 (d, J=4.9 Hz, 2H), 4.44 (s, 4H); NMR 44.283, 53,852, 64,073, 76.227. |
Here is a chemical reaction formula: Reactants are m2_m3_m0_m1:C1(OCC(C)O1)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m3_m0_m1:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(OC)(OC)=O;0:C(C(C)O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A single stage transesterification of propylene carbonate and methanol to form dimethyl carbonate and propylene glycol was conducted in a manner similar to that set forth in Example 1. The single stage experiment was conducted by combining a stream containing 61.25 weight percent of propylene carbonate and 38.76 weight percent of methanol with the potassium carbonate catalyst in a glass reaction tube. The results of the single stage transesterification of propylene carbonate and methanol are presented in Table 1. |
Here is a chemical reaction formula: Reactants are m2:CC#CC, amount is: 20.0 MILLIMOLE;m1:N1BNBNB1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m3:[C-]#[O+].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.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Rh], amount is: 0.0 .Products are 0:C(=CCC)B1NBNBN1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: As in the previous examples, borazine (1.618 g, 20.1 mmol) and 2-butyne (20 mmol) were reacted in the presence of RhH(CO)(PPh3)3 (0.0165 g, 0.018 mmol) for four hours at room temperature. Fractionation of the resulting reaction mixture gave 0.2702 g (2.01 mmol) of B-butenyl-borazine stopping in a -55° C. trap. GLC analysis of the product indicates that it is composed of a 3:2 mixture of B-trans-(2-cis-butenyl)borazine and B-trans(1-butenyl)borazine. Pure samples of each isomer were prepared by preparative G.L.C. |
Here is a chemical reaction formula: Reactants are m3:C(C)(=O)OCCCC(=O)ON(C(C)=O)C=1C(=C(C(=C(C(=O)N(CC(COC(C)=O)OC(C)=O)CC(COC(C)=O)OC(C)=O)C1I)I)C(=O)N)I, amount is: 0.0 MOLE;m2:C(C)(=O)OCC(=O)NC=1C(=C(C(=C(C(=O)NCC(COC(C)=O)OC(C)=O)C1I)I)C(=O)NCC(COC(C)=O)OC(C)=O)I, 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(CO)N(C=1C(=C(C(=C(C1I)C(=O)NCC(CO)O)I)C(=O)NCC(CO)O)I)C(=O)CO;0:OC(CNC(C1=C(C(C(=O)NCC(CO)O)=C(C(=C1I)NC(CO)=O)I)I)=O)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: ) acid hydrolyzing said 5-acetoxyacetamido-N,N'-bis(2,3-diacetoxypropyl)2,4,6-triiodoisophthalamide and 5-[N-(2-acetoxyethyl)acetoxyacetamido]-N,N-bis(2,3-diacetoxypropyl)-2,4,6-triiodoisophthalamide under acid hydrolyzing conditions to produce ioversol and N,N'-bis-(2,3-dihydroxypropyl)-5-glycolamido-2,4,6-triiodoisophthalamide; and |
Here is a chemical reaction formula: Reactants are m1_m5_m2_m6:C1(=CC=CC=C1)N(C(C)=O)C1=CC=CC=C1, amount is: 0.0 ;m1_m5_m2_m6:C(C)(C)[N-]C(C)C.[Li+], amount is: 0.0 MOLE;m4:Cl, amount is: 0.0 ;m3_m7:C(#N)C[C@H](CC(=O)OCC)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m6:O1CCCC1, amount is: 0.0 ;m1_m5_m2_m6:O1CCCC1.CCCCCCC, amount is: 0.0 ;m3_m7:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C[C@H](CC(CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred -10° C. solution of N,N-diphenylacetamide (211 g, 1.0 mol) in tetrahydrofuran (1.0 L) is slowly added a solution of lithium diisopropylamide in tetrahydrofuran-heptane (0.5 L of 2M) while maintaining the temperature between -10° C. to -5° C. The mixture is stirred at -0° C. to 20° C. for 30 minutes. (R)-4-cyano-3-hydroxybutyric acid, ethyl ester (Brower, supra) (40 g, 0.25 mol) as a solution in 200 mL of tetrahydrofuran is added to the previously prepared anion. The reaction mixture is stirred for 30 minutes at -5° C. to -20° C., and transferred to a 2.2N aqueous hydrochloric acid solution (1 L). The aqueous layer is extracted with 500 mL of ethyl acetate, the aqueous layer is separated and reextracted with 100 mL of ethyl acetate, the extracts are combined and concentrated in vacuo to afford crude (R)-6 -cyano-5-hydroxy-3-oxo-N,N-diphenylhexanamide which is not isolated. A small sample is purified by column chromatography on flash silica gel (60:40 hexane:ethyl acetate) as an oil. |
Here is a chemical reaction formula: Reactants are m1_m2:C(#N)CC(CC(CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)O)O, amount is: 0.0 MOLE;m1_m2:COC(C)(C)OC, amount is: 0.0 ;m3:CS(=O)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Crude [R-(R*,R*)]-6-cyano-3,5-dihydroxy-N,N-diphenylhexanamide, approximately 0.18 mol, is dissolved in 2,2-dimethoxypropane (160 mL, 1.5 mol) and acetone (300 mL). Methanesulfonic acid (0.5 mL) is added, and the solution is stirred for 2 hours at room temperature. The reaction is quenched by the addition of aqueous sodium bicarbonate (800 mL) and ethyl acetate (500 mL). The ethyl acetate solution is concentrated by vacuum distillation to give 62.5 g of (4R-cis)-6-(cyanomethyl)-2,2-dimethyl-N,N-diphenyl -1,3-dioxane-4-acetamide as an off-white crystalline solid (mp 98°-100° C., uncorrected). |
Here is a chemical reaction formula: Reactants are m4:[H][H], amount is: 0.0 MOLE;m1_m5_m2:C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m5_m2:N, amount is: 0.0 ;m3_m6:[H][H], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m2:CO, amount is: 0.0 ,Catalysts are m3_m6:[Ni], amount is: 0.0 MOLE.Products are 0:NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (4R-cis)-6-(cyanomethyl) -2,2-dimethyl-N,N-diphenyl-1,3-dioxane-4-acetamide (10.0 g, 0.027 mol) in methanol (150 mL) containing anhydrous ammonia (2.25 g) is reacted with hydrogen gas in a Parr shaker at 30° C. in the presence of a slurry of Raney nickel A-7000 (3.8 g). After 3 hours, uptake of hydrogen has ceased, the mixture is cooled to 20° C., the atmosphere is vented and exchanged for nitrogen, the slurry is filtered through celite, and concentrated at reduced pressure to give 9.5 g of (4R-cis) -6-(2-aminoethyl)-2,2-dimethyl-N,N-diphenyl-1,3-dioxane -4-acetamide as an oil. |
Here is a chemical reaction formula: Reactants are m2:Cl, amount is: 0.0 ;m1_m3:C1(=CC=CC=C1)N(C(C[C@H]1C[C@H](OC(O1)(C)C)CCN1C(=C(C(=C1C1=CC=C(C=C1)F)C1=CC=CC=C1)C(=O)NC1=CC=CC=C1)C(C)C)=O)C1=CC=CC=C1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC=C(C=C1)C1=C(C(=C(N1CCC(CC(CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)O)O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (4R-cis)-1-[2-[6-[2-(diphenylamino)-2-oxoethyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]-5-(4-fluorophenyl) -2-(1-methylethyl)-N,4-diphenyl-1H-pyrrole-3-carboxamide is dissolved in methanol (300 mL) and reacted by adding 1.0N hydrochloric acid (100 mL) and stirring for 12 hours at room temperature. The white crystalline solid [R-(R*,R*)]-5-(4-fluorophenyl) -β,δ-dihydroxy -2-(1-methylethyl)-N,N,4-triphenyl-3-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanamide is isolated by filtration (mp 228.5°-232.9° C., uncorrected). |
Here is a chemical reaction formula: Reactants are m3_m7:C(#N)C[C@H](CC(=O)OCC)O, amount is: 0.0 ;m1_m5_m2_m6:C1(=CC=CC=C1)CN(C(C)=O)CC1=CC=CC=C1, amount is: 0.0 ;m1_m5_m2_m6:C(C)(C)[N-]C(C)C.[Li+], amount is: 0.0 MOLE;m4:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m7:O1CCCC1, amount is: 0.0 ;m1_m5_m2_m6:O1CCCC1, amount is: 0.0 ;m1_m5_m2_m6:O1CCCC1.CCCCCCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C[C@H](CC(CC(=O)N(CC1=CC=CC=C1)CC1=CC=CC=C1)=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred -10° C. solution of N,N-bis(phenylmethyl)acetamide (prepared from N,N-bis(phenylmethyl)amine and acetyl chloride by refluxing for 2 hours in toluene) (120 g, 0.5 mol) in tetrahydrofuran (0.5 L) is slowly added a solution of lithium diisopropylamide in tetrahydrofuran-heptane (0.25 L of 2M) while maintaining the temperature between -30° C. to -45° C., and the mixture is stirred at -20° C. to -30° C. for 30 minutes. (R)-4-cyano-3-hydroxybutyric acid, ethyl ester (Brower, supra) (20 g, 0.125 mol) as a solution in 200 mL of tetrahydrofuran is then added to the previous mixture. The reaction mixture is stirred for 30 minutes at -35° C. to -20° C., and transferred to a 2.2N aqueous hydrochloric acid solution (0.5 L). The aqueous layer is extracted with 300 mL of ethyl acetate, the aqueous layer is separated and reextracted with 100 mL of ethyl acetate, the extracts are combined and concentrated in vacuo to afford crude (R)-6-cyano -5-hydroxy-3-oxo-N,N-bis(phenylmethyl)hexanamide as an oil. This oil, approximately 0.1 mol, is dissolved in tetrahydrofuran (200 mL) and methanol (100 mL) under a nitrogen atmosphere. The solution is cooled to -20° C., and a 50% solution of methoxydiethylborane in tetrahydrofuran (50 mL) is added. The reaction is cooled to -78° C., and sodium borohydride (12 g, 0.32 mol) is added over 30 minutes. The reaction is maintained at -78° C. for 5 hours and allowed to warm to room temperature and stand for 10 hours under a nitrogen atmosphere. The reaction is quenched by the addition of acetic acid (20 mL) and concentrated by vacuum distillation to an oil. The residue is dissolved with methanol (300 mL), concentrated by vacuum distillation, redissolved with methanol (300 mL), and reconcentrated by vacuum distillation to give a yellow oil. The oil is taken up in ethyl acetate (300 mL) and washed with deionized water (300 mL). The ethyl acetate solution is concentrated by vacuum distillation to give crude [R-(R*,R,)]-6-cyano-3,5-dihydroxy-N,N-bis(phenylmethyl)hexanamide as an oil which is used without further purification; |
Here is a chemical reaction formula: Reactants are m1_m5_m2:C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)N(CC1=CC=CC=C1)CC1=CC=CC=C1, amount is: 0.0 ;m1_m5_m2:N, amount is: 0.0 ;m3_m6:[H][H], amount is: 0.0 MOLE;m4:[H][H], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m2:CO, amount is: 0.0 ,Catalysts are m3_m6:[Ni], amount is: 0.0 MOLE.Products are 0:NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)N(CC1=CC=CC=C1)CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (4R-cis)-6-(cyanomethyl) -2,2-dimethyl-N,N-bis(phenylmethyl)-1,3-dioxane -4-acetamide (10.0 g, 0.025 mol) in methanol (150 mL) containing anhydrous ammonia (2.25 g) is reacted with hydrogen gas in a Parr shaker at 30° C. in a presence of a slurry of Raney nickel A-7000 (3.7 g). After hours, uptake of hydrogen has ceased, the mixture is cooled to 20° C., the atmosphere is vented and exchanged for nitrogen, the slurry is filtered through celite, and concentrated at reduced pressure to give 9.4 g of (4R-cis)-6-(2-aminoethyl)-2,2-dimethyl-N,N-bis(phenylmethyl) -1,3-dioxane-4-acetamide as an oil; |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 ;m3_m7:C(#N)C[C@H](CC(=O)OCC)O, amount is: 0.0 ;m1_m5_m2_m6:C(C)N(C(C)=O)CC, amount is: 0.0 ;m1_m5_m2_m6:C(C)(C)[N-]C(C)C.[Li+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m7:O1CCCC1, amount is: 0.0 ;m1_m5_m2_m6:O1CCCC1, amount is: 0.0 ;m1_m5_m2_m6:O1CCCC1.CCCCCCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C[C@H](CC(CC(=O)N(CC)CC)=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred -10° C. solution of N,N-diethylacetamide (prepared from N,N-diethylamine and acetyl chloride by refluxing for 2 hours in toluene) (28.75 g, 0.25 mol) in tetrahydrofuran (0.25 L) is slowly added a solution of lithium diisopropylamide in tetrahydrofuran-heptane (0.125 L of 2M) while maintaining the temperature between -10° C. to -50° C., and the mixture is stirred at -20° C. to 0° C. for 30 minutes. (R)-4-cyano-3-hydroxybutyric acid, ethyl ester (Brower, supra) (10 g, 0.06 mol) as a solution in 200 mL of tetrahydrofuran is added to the previously prepared mixture. The reaction mixture is stirred for 30 minutes at -5° C. to -20° C., and transferred to a 2.2N aqueous hydrochloric acid solution (0.25 L). The aqueous layer is extracted with 300 mL of ethyl acetate, the aqueous layer is separated and reextracted with 50 mL of ethyl acetate, the extracts are combined and concentrated in vacuo to afford crude (R)-6-cyano-N,N-diethyl-5-hydroxy-3-oxohexanamide as an oil; |
Here is a chemical reaction formula: Reactants are m1_m5_m2:C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)N(CC)CC, amount is: 0.0 ;m1_m5_m2:N, amount is: 0.0 ;m3_m6:[H][H], amount is: 0.0 MOLE;m4:[H][H], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m2:CO, amount is: 0.0 ,Catalysts are m3_m6:[Ni], amount is: 0.0 MOLE.Products are 0:NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)N(CC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (4R-cis)-6-(cyanomethyl) -N,N-diethyl-2,2-dimethyl-1,3-dioxane-4-acetamide (10.0 g, 0.037 mol) in methanol (220 mL) containing anhydrous ammonia (3.25 g) is reacted with hydrogen gas in a Parr shaker at 30° C. in a presence of a slurry of Raney nickel A-7000 (4.2 g). After 3 hours, uptake of hydrogen has ceased, the mixture is cooled to 20° C., the atmosphere is vented and exchanged for nitrogen, the slurry is filtered through celite, and concentrated at reduced pressure to give 9.2 g of (4R-cis)-6-(2-aminoethyl)-N,N-diethyl-2,2-dimethyl -1,3-dioxane-4-acetamide as an oil. |
Here is a chemical reaction formula: Reactants are m3_m6:C(#N)C[C@H](CC(=O)OCC)O, amount is: 0.0 ;m3_m6:O1CCCC1, amount is: 0.0 MOLE;m1_m5_m2_m7:C1(=CC=CC=C1)CNC(C)=O, amount is: 0.0 ;m1_m5_m2_m7:C(C)(C)[N-]C(C)C.[Li+], amount is: 0.0 MOLE;m1_m5_m2_m7:O1CCCC1, amount is: 0.0 ;m4:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m7:O1CCCC1.CCCCCCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C[C@H](CC(CC(=O)N(CC1=CC=CC=C1)C(C)(C)C)=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred -10° C. solution of N-1,1-dimethylethyl, N-phenylmethylacetamide (prepared from N-1,1-dimethylethyl, N-phenylmethyl amine, and acetyl chloride by refluxing for 2 hours in toluene) (102.5 g, 0.5 mol) in tetrahydrofuran (0.5 L) is slowly added a solution of lithium diisopropylamide in tetrahydrofuran-heptane (0.25 L of 2M) while maintaining the temperature between -40° C. to -50° C., and the mixture is stirred at -20° C. to -30° C. for 30 minutes. (R)-4-cyano-3-hydroxybutyric acid, ethyl ester (Brower, supra) (20 g, 0.125 mol) as a solution in 200 mL or tetrahydrofuran is then added to the previous mixture. The reaction mixture is stirred for 30 minutes at -25° C. to -20° C., and transferred to a 2.2N aqueous hydrochloric acid solution (0.5 L). The aqueous layer is extracted with 300 mL of ethyl acetate, the aqueous layer is separated and reextracted with 100 mL of ethyl acetate, the extracts are combined and concentrated in vacuo to afford crude (R)-6-cyano-N-(1,1-dimethylethyl) -5-hydroxy-3-oxo-N-(phenylmethyl) hexanamide as an oil. |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 MOLE;m1_m5_m2_m7:C(C)(=O)N1CCCCC1, amount is: 0.0 ;m1_m5_m2_m7:C(C)(C)[N-]C(C)C.[Li+], amount is: 0.0 MOLE;m1_m5_m2_m7:O1CCCC1, amount is: 0.0 ;m3_m6:C(#N)C[C@H](CC(=O)OCC)O, amount is: 0.0 ;m3_m6:O1CCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m7:O1CCCC1.CCCCCCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O[C@H](CC(CC(C#N)=O)=O)CN1CCCCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred -10° C. solution of 1-acetylpiperidine (127 g, 1.0 mol) in tetrahydrofuran (1.0 L) is slowly added a solution of lithium diisopropylamide in tetrahydrofuran-heptane (0.5 L of 2M) while maintaining the temperature between -40° C. to -50° C., and the mixture is stirred at -20° C. to -30° C. for 30 minutes. (R)-4-cyano-3-hydroxybutyric acid, ethyl ester (Brower, supra) (40 g, 0.25 mol) as a solution in 200 mL of tetrahydrofuran is then added to the previous mixture. The reaction mixture is stirred for 30 minutes at -25° C. to -20° C., and transferred to a 2.2N aqueous hydrochloric acid solution (1L). The aqueous layer is extracted with 500 mL of ethyl acetate, the aqueous layer is separated and extracted with 100 mL of ethyl acetate, the extracts are combined and concentrated in vacuo to afford (R)-ε-hydroxy-α,γ-dioxo -1-piperidineheptanenitrile as an oil. |
Here is a chemical reaction formula: Reactants are m1_m2:C(CC)(=O)C1=CC=CC=C1, amount is: 0.0 ;m1_m2:C(C)(=O)OC(C)=O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC=1C(C2=CC=CC=C2C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of propiophenone (30 g, 223.6 mmol) hexamethylenetetramine (HMTA) (43.8 g, 313 mmol) and acetic anhydride (41 g, 402 mmol) was heated at 80° C. for 4 hours under a nitrogen atmosphere. The reaction mixture was cooled to 30° C. and quenched into a stirred mixture of methylene chloride (200 ml) and sodium hydroxide (200 of 2N solution). The organic layer was separated and washed with aqueous HCl (100 ml of 1N solution). The methylene chloride solution containing the product, 2-methyl-1-phenyl-prop-2-en-1-one was azeotropically dried by distilling CH2Cl2 to approximately 50 ml volume and was directly used in the next step without any further operation. The CH2Cl2 solution was added to concentrated H2SO4 (130 ml) at such a rate that the reaction temperature was maintained between 50°-60° C. The CH2Cl2 was removed by distillation and nitrogen sweep as soon as it was added. The reaction mixture was stirred at 50°-60° C. for one hour, cooled to 20° C. and quenched into a stirred mixture of methylene chloride (200 ml) and water (200 g). After separating the aqueous layer, the organic layer was concentrated in the rotary evaporator to produce 121 g (82%) of 2-methyl-inden-1-one (Example 1, Table 1). |
Here is a chemical reaction formula: Reactants are m2:Cl, amount is: 0.0 ;m1:CNC1=CC(=CC=C1)CC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3:CCOCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)C=1C=C(N)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The N-methyl-3-ethyl aniline obtained in the previous step was dissolved in 250 ml anhydrous ether and to this was added (by annulation) about 400 ml of HCl (1.0M solution in ether) at ambient temperature. The resultant white precipitate was filtered through a Buchner funnel, washed with ether, and dried to afford 39.0 g (95% yield, 76% overall in 3 steps from 3-ethyl aniline) of a white solid. |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 ;m1_m5_m2_m6:C1(=CC=CC=C1)N(C(C)=O)C1=CC=CC=C1, amount is: 0.0 ;m1_m5_m2_m6:C(C)(C)[N-]C(C)C.[Li+], amount is: 0.0 MOLE;m3_m7:C(#N)C[C@H](CC(=O)OCC)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m6:O1CCCC1, amount is: 0.0 ;m1_m5_m2_m6:O1CCCC1.CCCCCCC, amount is: 0.0 ;m3_m7:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C[C@H](CC(CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred -10° C. solution of N,N-diphenylacetamide (211 g, 1.0 mol) in tetrahydrofuran (1.0 L) is slowly added a solution of lithium diisopropylamide in tetrahydrofuran-heptane (0.5 L of 2M) while maintaining the temperature between -10° C. to -5° C. The mixture is stirred at -0° C. to 20° C. for 30 minutes. (R)-4-cyano-3-hydroxybutyric acid, ethyl ester (Brower, supra) (40 g, 0.25 mol) as a solution in 200 mL of tetrahydrofuran is added to the previously prepared anion. The reaction mixture is stirred for 30 minutes at -5° C. to -20° C., and transferred to a 2.2N aqueous hydrochloric acid solution (1 L). The aqueous layer is extracted with 500 mL of ethyl acetate, the aqueous layer is separated and reextracted with 100 mL of ethyl acetate, the extracts are combined and concentrated in vacuo to afford crude (R)-6 -cyano-5-hydroxy-3-oxo-N,N-diphenylhexanamide which is not isolated. A small sample is purified by column chromatography on flash silica gel (60:40 hexane:ethyl acetate) as an oil. Proton nuclear magnetic resonance spectroscopy |
Here is a chemical reaction formula: Reactants are m1_m2:C(#N)CC(CC(CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)O)O, amount is: 0.0 MOLE;m1_m2:COC(C)(C)OC, amount is: 0.0 ;m3:CS(=O)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Crude [R-(R*,R*)]-6-cyano-3,5-dihydroxy-N,N-diphenylhexanamide, approximately 0.18 mol, is dissolved in 2,2-dimethoxypropane (160 mL, 1.5 mol) and acetone (300 mL). Methanesulfonic acid (0.5 mL) is added, and the solution is stirred for 2 hours at room temperature. The reaction is quenched by the addition of aqueous sodium bicarbonate (800 mL) and ethyl acetate (500 mL). The ethyl acetate solution is concentrated by vacuum distillation to give 62.5 g of (4R-cis)-6-(cyanomethyl)-2,2-dimethyl-N,N-diphenyl-1,3-dioxane-4-acetamide as an off-white crystalline solid (mp 98°-100° C., uncorrected). |
Here is a chemical reaction formula: Reactants are m3_m6:[H][H], amount is: 0.0 MOLE;m4:[H][H], amount is: 0.0 MOLE;m1_m5_m2:C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m5_m2:N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:CO, amount is: 0.0 ,Catalysts are m3_m6:[Ni], amount is: 0.0 MOLE.Products are 0:NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (4R-cis)-6-(cyanomethyl)-2,2-dimethyl-N,N-diphenyl-1,3-dioxane-4-acetamide (10.0 g, 0.027 mol) in methanol (150 mL) containing anhydrous ammonia (2.25 g) is reacted with hydrogen gas in a Parr shaker at 30° C. in the presence of a slurry of Raney nickel A-7000 (3.8 g). After 3 hours, uptake of hydrogen has ceased, the mixture is cooled to 20° C., the atmosphere is vented and exchanged for nitrogen, the slurry is filtered through celite, and concentrated at reduced pressure to give 9.5 g of (4R-cis)-6-(2-aminoethyl)-2,2-dimethyl-N,N-diphenyl-1,3-dioxane-4-acetamide as an oil. |
Here is a chemical reaction formula: Reactants are m1_m3:C1(=CC=CC=C1)N(C(C[C@H]1C[C@H](OC(O1)(C)C)CCN1C(=C(C(=C1C1=CC=C(C=C1)F)C1=CC=CC=C1)C(=O)NC1=CC=CC=C1)C(C)C)=O)C1=CC=CC=C1, amount is: 0.0 MOLE;m1_m3:CO, amount is: 0.0 ;m2:Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC1=CC=C(C=C1)C1=C(C(=C(N1CCCC(C(CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)O)O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (4R-cis)-1-[2-[6-[2-(diphenylamino)-2-oxoethyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1H-pyrrole-3-carboxamide is dissolved in methanol (300 mL) and reacted by adding 1.0N hydrochloric acid (100 mL) and stirring for 12 hours at room temperature. The white crystalline solid [R-(R*,R*)]-5-(4-fluorophenyl)-β,γ-dihydroxy-2-(1-methylethyl)-N,N,4-triphenyl-3-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanamide is isolated by filtration (mp 228.5°-232.9° C., uncorrected). FTIR (KBr) 3400 (broad), 2850, 1640 cm-1 ; |
Here is a chemical reaction formula: Reactants are m1_m5_m2_m6:C1(=CC=CC=C1)CN(C(C)=O)CC1=CC=CC=C1, amount is: 0.0 ;m1_m5_m2_m6:C(C)(C)[N-]C(C)C.[Li+], amount is: 0.0 MOLE;m4:Cl, amount is: 0.0 ;m3_m7:C(#N)C[C@H](CC(=O)OCC)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m6:O1CCCC1, amount is: 0.0 ;m1_m5_m2_m6:O1CCCC1.CCCCCCC, amount is: 0.0 ;m3_m7:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C[C@H](CC(CC(=O)N(CC1=CC=CC=C1)CC1=CC=CC=C1)=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred -10° C. solution of N,N-bis(phenylmethyl)acetamide (prepared from N, N-bis(phenylmethyl)amine and acetyl chloride by refluxing for 2 hours in toluene) (120 g, 0.5 mol) in tetrahydrofuran (0.5 L) is slowly added a solution of lithium diisopropylamide in tetrahydrofuran-heptane (0.25 L of 2M) while maintaining the temperature between -30° C. to -45° C., and the mixture is stirred at -20° C. to -30° C. for 30 minutes. (R)-4-cyano-3-hydroxybutyric acid, ethyl ester (Brower, supra) (20 g, 0.125 mol) as a solution in 200 mL of tetrahydrofuran is then added to the previous mixture. The reaction mixture is stirred for 30 minutes at -35° C. to -20° C., and transferred to a 2.2N aqueous hydrochloric acid solution (0.5 L). The aqueous layer is extracted with 300 mL of ethyl acetate, the aqueous layer is separated and reextracted with 100 mL of ethyl acetate, the extracts are combined and concentrated in vacuo to afford crude (R)-6-cyano-5-hydroxy-3-oxo-N,N-bis(phenylmethyl)hexanamide as an oil. This oil, approximately 0.1 mol, is dissolved in tetrahydrofuran (200 mL) and methanol (100 mL) under a nitrogen atmosphere. The solution is cooled to -20° C., and a 50% solution of methoxydiethylborane in tetrahydrofuran (50 mL) is added. The reaction is cooled to -78° C., and sodium borohydride (12 g, 0.32 mol) is added over 30 minutes. The reaction is maintained at -78° C. for 5 hours and allowed to warm to room temperature and stand for 10 hours under a nitrogen atmosphere. The reaction is quenched by the addition of acetic acid (20 mL) and concentrated by vacuum distillation to an oil. The residue is dissolved with methanol (300 mL), concentrated by vacuum distillation, redissolved with methanol (300 mL), and reconcentrated by vacuum distillation to give a yellow oil. The oil is taken up in ethyl acetate (300 mL) and washed with deionized water (300 mL). The ethyl acetate solution is concentrated by vacuum distillation to give crude [R-(R*,R*)]-6-cyano-3,5-dihydroxy-N,N-bis(phenylmethyl)hexanamide as an oil which is used without further purification; |
Here is a chemical reaction formula: Reactants are m3_m6:[H][H], amount is: 0.0 MOLE;m1_m5_m2:C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)N(CC1=CC=CC=C1)CC1=CC=CC=C1, amount is: 0.0 ;m1_m5_m2:N, amount is: 0.0 ;m4:[H][H], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m2:CO, amount is: 0.0 ,Catalysts are m3_m6:[Ni], amount is: 0.0 MOLE.Products are 0:NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)N(CC1=CC=CC=C1)CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (4R-cis)-6-(cyanomethyl)-2,2-dimethyl-N,N-bis(phenylmethyl)-1,3-dioxane-4-acetamide (10.0 g, 0.025 mol) in methanol (150 mL) containing anhydrous ammonia (2.25 g) is reacted with hydrogen gas in a Parr shaker at 30° C. in a presence of a slurry of Raney nickel A-7000 (3.7 g). After 3 hours, uptake of hydrogen has ceased, the mixture is cooled to 20° C., the atmosphere is vented and exchanged for nitrogen, the slurry is filtered through celite, and concentrated at reduced pressure to give 9.4 g of (4R-cis)-6-(2-aminoethyl)-2,2 -dimethyl-N,N-bis(phenylmethyl)-1,3-dioxane-4-acetamide as an oil; |
Here is a chemical reaction formula: Reactants are m3_m7:C(#N)C[C@H](CC(=O)OCC)O, amount is: 0.0 ;m4:Cl, amount is: 0.0 ;m1_m5_m2_m6:C(C)N(C(C)=O)CC, amount is: 0.0 ;m1_m5_m2_m6:C(C)(C)[N-]C(C)C.[Li+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m7:O1CCCC1, amount is: 0.0 ;m1_m5_m2_m6:O1CCCC1, amount is: 0.0 ;m1_m5_m2_m6:O1CCCC1.CCCCCCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C[C@H](CC(CC(=O)N(CC)CC)=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred -10° C. solution of N,N-diethylacetamide (prepared from N,N-diethylamine and acetyl chloride by refluxing for 2 hours in toluene) (28.75 g, 0.25 mol) in tetrahydrofuran (0.25 L) is slowly added a solution of lithium diisopropylamide in tetrahydrofuran-heptane (0.125 L of 2M) while maintaining the temperature between -10° C. to -5° C., and the mixture is stirred at -20° C. to 0° C. for 30 minutes. (R)-4-cyano-3-hydroxybutyric acid, ethyl ester (Brower, supra) (10 g, 0.06 mol) as a solution in 200 mL of tetrahydrofuran is added to the previously prepared mixture. The reaction mixture is stirred for 30 minutes at -5° C. to -20° C., and transferred to a 2.2N aqueous hydrochloric acid solution (0.25 L). The aqueous layer is extracted with 300 mL of ethyl acetate, the aqueous layer is separated and reextracted with 50 mL of ethyl acetate, the extracts are combined and concentrated in vacuo to afford crude (R)-6-cyano-N,N-diethyl-5-hydroxy-3-oxohexanamide as an oil; |
Here is a chemical reaction formula: Reactants are m1_m5_m2:C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)N(CC)CC, amount is: 0.0 ;m1_m5_m2:N, amount is: 0.0 ;m3_m6:[H][H], amount is: 0.0 MOLE;m4:[H][H], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m2:CO, amount is: 0.0 ,Catalysts are m3_m6:[Ni], amount is: 0.0 MOLE.Products are 0:NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)N(CC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (4R-cis)-6-(cyanomethyl)-N,N-diethyl-2,2-dimethyl-1,3-dioxane-4-acetamide (10.0 g, 0,037 mol) in methanol (220 mL) containing anhydrous ammonia (3.25 g) is reacted with hydrogen gas in a Parr shaker at 30° C. in a presence of a slurry of Raney nickel A- 7000 (4.2 g) . After 3 hours, uptake of hydrogen has ceased, the mixture is cooled to 20° C., the atmosphere is vented and exchanged for nitrogen, the slurry is filtered through celite, and concentrated at reduced pressure to give 9.2 g of (4R-cis)-6-(2-aminoethyl)-N,N-diethyl-2,2-dimethyl-1,3-dioxane-4-acetamide as an oil. |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 ;m3_m6:C(#N)C[C@H](CC(=O)OCC)O, amount is: 0.0 ;m3_m6:O1CCCC1, amount is: 0.0 MOLE;m1_m5_m2_m7:C1(=CC=CC=C1)CNC(C)=O, amount is: 0.0 ;m1_m5_m2_m7:C(C)(C)[N-]C(C)C.[Li+], amount is: 0.0 MOLE;m1_m5_m2_m7:O1CCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m7:O1CCCC1.CCCCCCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C[C@H](CC(CC(=O)N(CC1=CC=CC=C1)C(C)(C)C)=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred -10° C. solution of N-1,1-dimethylethyl, N-phenylmethylacetamide (prepared from N-1,1-dimethylethyl, N-phenylmethyl amine, and acetyl chloride by refluxing for 2 hours in toluene) (102.5 g, 0.5 mol) in tetrahydrofuran (0.5 L) is slowly added a solution of lithium diisopropylamide in tetrahydrofuran-heptane (0.25 L of 2M) while maintaining the temperature between -40° C. to -50° C., and the mixture is stirred at -20° C. to -30° C. for 30 minutes. (R)-4-cyano-3-hydroxybutyric acid, ethyl ester (Brower, supra) (20 g, 0.125 mol) as a solution in 200 mL or tetrahydrofuran is then added to the previous mixture. The reaction mixture is stirred for 30 minutes at -25° C. to -20° C., and transferred to a 2.2N aqueous hydrochloric acid solution (0.5 L). The aqueous layer is extracted with 300 mL of ethyl acetate, the aqueous layer is separated and reextracted with 100 mL of ethyl acetate, the extracts are combined and concentrated in vacuo to afford crude (R)-6-cyano-N-(1,1-dimethylethyl)-5-hydroxy-3-oxo-N-(phenylmethyl)hexanamide as an oil. |
Here is a chemical reaction formula: Reactants are m3_m6:C(#N)C[C@H](CC(=O)OCC)O, amount is: 0.0 ;m3_m6:O1CCCC1, amount is: 0.0 ;m4:Cl, amount is: 0.0 ;m1_m5_m2_m7:C(C)(=O)N1CCCCC1, amount is: 0.0 ;m1_m5_m2_m7:C(C)(C)[N-]C(C)C.[Li+], amount is: 0.0 MOLE;m1_m5_m2_m7:O1CCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m7:O1CCCC1.CCCCCCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O[C@H](CC(CC(C#N)=O)=O)CN1CCCCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred -10° C. solution of 1-acetylpiperidine (127 g, 1.0 mol) in tetrahydrofuran (1.0 L) is slowly added a solution of lithium diisopropylamide in tetrahydrofuran-heptane (0.5 L of 2M) while maintaining the temperature between -40° C. to -50° C., and the mixture is stirred at -20° C. to -30° C. for 30 minutes. (R)-4-cyano-3-hydroxybutyric acid, ethyl ester (Brower, supra) (40 g, 0.25 mol) as a solution in 200 mL of tetrahydrofuran is then added to the previous mixture. The reaction mixture is stirred for 30 minutes at -25° C. to -20° C., and transferred to a 2.2N aqueous hydrochloric acid solution (1 L). The aqueous layer is extracted with 500 mL of ethyl acetate, the aqueous layer is separated and extracted with 100 mL of ethyl acetate, the extracts are combined and concentrated in vacuo to afford (R)-ε-hydroxy-α,γ-dioxo-1-piperidineheptanenitrile as an oil. |
Here is a chemical reaction formula: Reactants are m2:S(O)(O)(=O)=O, amount is: 0.0 ;m6_m0:C(C)#N, amount is: 0.0 MOLE;m1_m5:[C@@H]1([C@@H](CC2=CC=CC=C12)O)O, amount is: 0.0 ;m1_m5:C(C)#N, amount is: 0.0 ;m4:[OH-].[Na+], amount is: 0.0 MOLE;m3: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:N[C@H]1[C@H](CC2=CC=CC=C12)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Trans-1,2-indandiol (1.5 g) was dissolved in acetonitrile (25 mL) cooled to 0° C., and concentrated sulfuric acid (1.1 mL) was added. The mixture was gradually warmed to 20° C. and aged to 3 hours. Water (2 mL) was added and the mixture heated to reflux. Concentrated aqueous sodium hydroxide was added to adjust the pH to 12. The resulting solid was removed by filtration to provide an aqueous acetonitrile solution of cis-1 -amino-2-indanol (1.02 g, 63 % yield). |
Here is a chemical reaction formula: Reactants are m2:S(O)(O)(=O)=O, amount is: 0.0 ;m1_m4:[C@@H]1([C@H](CC2=CC=CC=C12)O)O, amount is: 0.0 ;m1_m4:C(C)#N, amount is: 0.0 ;m3:O, 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:N[C@H]1[C@H](CC2=CC=CC=C12)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Cis-1,2-indandiol (1.0 g) was dissolved in acetonitrile (20 mL), cooled to -40° C., and fuming sulfuric acid (21% SO3, 0.8 mL) was added. The mixture was aged for 1 hour with gradual warming to 0° C. Water was added and the mixture heated to 80° C. for 1 hour to provide an aqueous solution of cis-1-amino-2-indanol. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5_m4_m6:CC1=C(C=C(C=C1)Br)C, amount is: 0.0 ;m1_m2_m3_m5_m4_m6:C1(=CC=CC2=CC=CC=C12)B(O)O, amount is: 0.0 ;m1_m2_m3_m5_m4_m6:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5_m4_m6:CN(C=O)C, amount is: 0.0 ,Catalysts are m1_m2_m3_m5_m4_m6:C(C)(=O)[O-].C(C)(=O)[O-].[Pd+2], amount is: 0.0 ;m1_m2_m3_m5_m4_m6:C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C, amount is: 0.0 .Products are 0:CC=1C=C(C=C(C1)C)C1=CC=CC2=CC=CC=C12, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of dimethyl-5-bromobenzene (1.85 g, 10 mmol), 1-naphthalene boronic acid (1.89 g, 11 mmol), triethylamine (2.8 mL, 20 mmol), tris-(2-tolyl)phosphine (0.125 g, 0.4 mmol), palladium (II) diacetate (0.045 g, 0.4 mmol) and anhydrous dimethylformamide (25 mL) with 5 Å molecular sieves (0.5g) was stirred at 100° C. under a nitrogen atmosphere for about 4 hours. The solvent was evaporated in vacuo and the residue was treated with 5% aqueous ammonia solution, extracted with ethyl acetate, and washed with saturated aqueous sodium chloride. After filtration to remove a black precipitate, the organic layer was dried over magnesium sulfate, filtered and evaporated. The yellowish oil residue was chromatographed on silica gel (methylene chloride;petroleum ether 1:2 as eluant) to give a colorless oil (1.7 g, 7.3 mmol) in 73% yield. This crystallized upon standing (mp 68-70° C.). |
Here is a chemical reaction formula: Reactants are m2:C(Cl)Cl, amount is: 0.0 MOLE;m4:N#N, amount is: 0.0 MOLE;m5_m7:[Al+3].[Cl-].[Cl-].[Cl-], amount is: 0.0 MOLE;m5_m7:C(CCC)Cl, amount is: 0.0 MOLE;m3:[Al+3].[Cl-].[Cl-].[Cl-], amount is: 0.0 ;m0_m1_m8:C(CCC)Cl, amount is: 0.0 ;m6:C(CCC)Cl, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C=CCCCCCC;0:C=CCCCCCCCCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A two liter reactor is equipped with a stirrer, addition funnel, thermometer, condenser and a cooling bath. A solution of 300 g (2.68 moles) 1-octene, 300 g (1.79 moles) 1-dodecene and 3.9 g (0.042 moles) normal butyl chloride was prepared and charged to the addition funnel. To the reactor was charged 300 ml. dry methylene chloride and 12.0 g anhydrous AlCl3. A N2 atmosphere was maintained throughout the polymerization procedure. The stirred AlCl3 slurry was cooled to 15° C., whereupon a dropwise addition of the comonomer/n-butyl chloride solution was initiated and continued over 3.0 hours into the reactor. The polymerization temperature was maintained at 15° C.±1° C. After the comonomer/n-butyl chloride charge was complete, the polymerization mixture was stirred for an additional 3.0 hours at 15° C. |
Here is a chemical reaction formula: Reactants are m2_m3:C(=O)([O-])C(O)C(O)C(=O)[O-].[Na+].[Na+], amount is: 0.0 ;m2_m3:[N+](=O)([O-])[O-].[Ag+], amount is: 0.0 ;m1:[Ag], 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(=O)([O-])C(O)C(O)C(=O)[O-].[Ag+2], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: This example illustrates the preparation of the silver coating solutionthat is used in Examples 4 and 5. 3 ml of a sodium tartrate solution (1 g tartaric acid disodium salt dihydrate (obtained from Aldrich) dissolved in20 ml distilled water) was added to 3 ml of a silver nitrate solution (10 gsilver nitrate dissolved in 10 ml distilled water) at 22° C. A whiteprecipitate of silver tartrate formed rapidly. Concentrated ammonium hydroxide, 28% ammonia (obtained from EM Science), was added dropwise to the solution until the silver tartrate dissolved completely to give a clear solution of ammonical silver tartarate with a pH of approximately 12. |
Here is a chemical reaction formula: Reactants are m5_m2:C(C=C)Cl, amount is: 0.0 MOLE;m3:C[Si](C)(C)Cl, amount is: 2.8399999141693115 MILLIMOLE;m1:ClC1C=CCCC1, amount is: 3.200000047683716 MILLIMOLE;m4:C1(C=CCCC1)=O, amount is: 0.8199999928474426 MILLIMOLE,this reaction does not need reagents,Solvents are m5_m2:C1CCOC1, amount is: 0.0 ;m6:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(C=CCCC1)C1CC(CCC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In an effort to diminish homocoupling, 3-chlorocyclohexene (3.20 mmol) was weighed in a large vial and capped with a septum. Once under an argon atmosphere, THF (10 ml) was added to the vial. To a stirring active coppersolution (8.23 mmol in 23 ml of THF) at -95° C., the allyl chloride is delivered dropwise from a cannula, over 30 minutes. After 5 minutes, TMSCl (2.84 mmol) is injected neat prior to the neat, dropwise injection of 2-cyclohexenone (0.82 mmol). The reaction flask is placed in a -78° C. bath and allowed to gradually warm to room temperature. Thereaction mixture is quenched with NH4Cl (sat'd) (50 ml) and Et2O (25 ml) is added prior to further extraction of the organic layer with 0.5M HCl (50 ml), water (50 ml), and brine (50 ml). The combined aqueous layers are back extracted with Et2O (30 ml). The combined organic layers are dried with MgSO4 and reduced in volume for column chromatography. 3-(2-cyclohexenyl)cyclohexanone (0.43 mmol) was isolated in 52% yield (not shown in Table III). Rf =0.31 in 9:1 (v/v) hexane and ethyl acetate, respectively. 1H NMR (300 MHz) 5.73-5.67 (m, 1H),5.53-5.50 (m, 1H), 2.37-1.16 (m, 16H). 13C NMR (75 MHz) 212.50, 212.47, 129.1, 128.8, 128.7, 128.5, 45.2, 45.0, 43.6, 41.4, 40.0, 39.9, 28.4, 28.1, 25.52, 25.46, 25.41, 25.3, 25.2, 25.1, 21.8, 21.7. |
Here is a chemical reaction formula: Reactants are m1:C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)S(=O)(=O)Cl, amount is: 0.0 ;m2:CO, amount is: 0.0 ;m3:N1=CC=CC=C1, amount is: 0.0 ;m4:O, 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(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)S(=O)(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 10.0 g (32.4 mmol) of 3,5-di-t-butyl-4-hydroxybenzenesulfonyl chloride, prepared as described above, and 50 ml of anhydrous methanol was added 2.56 g (32.4 mmol) of pyridine. An exothermic reaction ensued resulting in a solution. The solution was stirred at room temperature for 30 minutes and poured into water. A white solid precipitate formed which was collected and dissolved in methylene chloride. The solution was washed with water, dried over magnesium sulfate and concentrated. The solid residue was recrystallized from heptane to give 7.66 g of, as a white crystalline product, methyl 3,5-di-tertiary-butyl-4-hydroxybenzenesulfonate (78.7% of theory); mp=116.5°-18° C. |
Here is a chemical reaction formula: Reactants are m2:N1=CC=CC=C1, amount is: 0.0 ;m3_m6:C1(=CC=CC=C1)O, amount is: 0.0 ;m1:C1=CC=CC2=NC3=CC=CC=C3C(=C12)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:S(=O)(Cl)Cl, amount is: 0.0 ;m3_m6:C(Cl)Cl, amount is: 0.0 MOLE;m5:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C1=CC=CC2=NC3=CC=CC=C3C(=C12)C(=O)OC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Acridine-9-carboxylic acid (1 g, 4.1 mmol) was suspended in thionyl chloride (5 mL) and the reaction mixture was refluxed for 3 hours. The solvent was removed under reduced pressure leaving a yellow solid which was dissolved in methylene chloride and pyridine (350 μL) under argon. This solution was cooled in an ice bath and a solution of phenol (0.78 g, 8.2 mmol) in methylene chloride was added dropwise. The reaction mixture was stirred overnight at room temperature. After evaporation of solvent, the residue was redissolved in ethyl acetate and washed with water. The organic layer was dried over MgSO4 and concentrated to obtain a crudematerial which was chromatographed on silica gel (30% ethyl acetate/hexane)to yield the pure product as a yellow solid. 1H NMR (CDCl3) δ7.35-7.57 (m, 5H), 7.63-8.37 (m, 8H). |
Here is a chemical reaction formula: Reactants are m2:FC(S(=O)(=O)OC)(F)F, amount is: 0.0 ;m1_m3:C1=CC=CC2=NC3=CC=CC=C3C(=C12)C(=O)OC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(S(=O)(=O)[O-])(F)F.C[N+]1=C2C=CC=CC2=C(C2=CC=CC=C12)C(=O)OC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenyl acridine-9-carboxylate (530 mg, 1.7 mmol) was dissolved in methylenechloride (5 mL) under argon and methyl trifluoromethanesulfonate (1 mL, 8.8mmol) was added. The solution was stirred overnight at room temperature to yield a thick yellow precipitate. This precipitate was filtered, washed with ether and dried to obtain the product as yellow crystals. 1H NMR (acetone-d6) δ5.22 (s, 3H), 7.47-7.71 (m, 5H), 8.23-9.07 (m, 8H). |
Here is a chemical reaction formula: Reactants are m3:N1C=NC=C1, amount is: 0.0 ;m1:C1(O)=CC=C(O)C=C1, amount is: 0.0 ;m2:[Si](C)(C)(C(C)(C)C)Cl, amount is: 0.0 ;m4:C(C)(=O)OCC.CCCCCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 ;m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OC1=CC=C(C=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of hydroquinone (1.0 g, 0.9 mmol) and tert-butyldimethylsilylchloride (1.4 g, 0.9 mmol) in 5 mL of dry DMF was gradually added imidazole(1.2 g, 1.8 mmol) and the solution was stirred for 1 hour. TLC analysis (silica gel, 20% ethyl acetate/hexane) showed completion of reaction. The solution was poured into 25 mL of water and extracted with 3×25 mL of ether. The combined ether solutions were dried over anhydrous MgSO4. Evaporation of solvent gave an oil which was chromatographed on silica using 20% ethyl acetate/hexane to give the product as a white solid in 70% yield: 1H NMR (CDCl3) δ0.145 (s, 6H), 0.956 (s, 9H), 4.47 (bs, 1H), 6.68 (s, 4H); 13C NMR (CDCl3) δ-4.48, 18.21, 25.74, 115.93, 120.55, 120.81, 149.78. |
Here is a chemical reaction formula: Reactants are m1:C1(O)=CC(O)=CC=C1, amount is: 0.0 ;m2:[Si](C)(C)(C(C)(C)C)Cl, amount is: 0.0 ;m3:N1C=NC=C1, amount is: 0.0 ;m4:C(C)(=O)OCC.CCCCCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:CN(C)C=O, amount is: 0.0 ;m6:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OC=1C=C(C=CC1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of resorcinol (1.0 g, 0.9 mmol) and tert-butyldimethylsilyl chloride (1.4 g, 0.9 mmol) in 5 mL of dry DMF was gradually added imidazole (1.2 g, 1.8 mmol) and the solution was stirred for 1 hour. TLC analysis (silica gel, 20% ethyl acetate/hexane) showed completion of reaction. The solution was poured into 25 mL of water and extracted with 3×25 mL of ether. The combined ether solutions were dried over anhydrous MgSO4. Evaporation of solvent gave an oil which was chromatographed on silica using 20% ethyl acetate/hexane to give the product as a white solid in 70% yield: 1H NMR (CDCl3) δ0.199 (s, 6H), 0.983 (s, 9H), 6.39-7.09 (m, 4H). |
Here is a chemical reaction formula: Reactants are m2:FC(S(=O)(=O)OC)(F)F, amount is: 0.0 ;m1_m4:C1(=CC=CC=C1)N(C(=O)C=1C2=CC=CC=C2N=C2C=CC=CC12)NS(=O)(=O)C1=CC=C(C=C1)C, amount is: 0.0 ;m3:CCCCCC, amount is: 0.0 MOLE,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:FC(S(=O)(=O)[O-])(F)F.C[N+]1=C2C=CC=CC2=C(C2=CC=CC=C12)C(=O)N(NS(=O)(=O)C1=CC=C(C=C1)C)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-Phenyl-N-(p-toluenesulfonamido)acridine-9-carboxamide (30 mg, 0.0068 mmol) was dissolved in methylene chloride (5 mL) under argon and methyl trifluoromethanesulfonate (77 μL, 0.068 mmol) was added. The solution was stirred overnight at room temperature to yield a yellow precipitate. Hexane was added and the precipitate filtered. Solid was further washed with ether and dried to obtain the product as yellow crystals. 1H NMR (acetone-d6) δ2.58 (s, 3H), 5.02 (s, 3H), 7.02-8.79 (m, 12H) . |
Here is a chemical reaction formula: Reactants are m1:FC(S(=O)(=O)[O-])(F)F.C[N+]1=C2C=CC=CC2=C(C2=CC=CC=C12)C(=O)N(NS(=O)(=O)C1=CC=C(C=C1)C)C1=CC=CC=C1, amount is: 0.0 ;m2:[Cl-].[NH4+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C(Cl)Cl, amount is: 0.0 MOLE;m3:C(C)O, amount is: 0.0 ,Catalysts are m5:[Zn], amount is: 0.0 ;m6:[Zn], amount is: 0.0 MOLE.Products are 0:CN1C=2C=CC=CC2C(C2=CC=CC=C12)C(=O)N(NS(=O)(=O)C1=CC=C(C=C1)C)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 10-Methyl-N-(phenyl)-N-(p-toluenesulfonamido)acridinium-9-carboxamide trifluoromethanesulfonate (10 mg, 0.0016 mmol) was suspended in absolute ethanol (10 mL) and solution was refluxed for 15 min to obtain a clear solution. Ammonium chloride (88 mg, 1.6 mmol) was added by portions to thesolution followed by zinc (108 mg, 1.6 mmol). The yellow color of solution disappeared immediately after the addition of zinc. Colorless solution wasrefluxed for 2 h. TLC of reaction mixture showed complete conversion to a non-polar material. Solution was filtered and precipitate was washed with ethanol (3×20 mL). Solution was concentrated to obtain an off-white solid which was redissolved in methylene chloride and washed with water (2×15 mL). Organic layer was dried over Na2SO4 and concentrated to yield the crude product which was purified by preparative TLC using (30% ethyl acetate:hexane) Pure product was obtained as an off-white solid. 1HNMR (CDCl3) δ2.40 (s, 3H), 3.18 (s, 3H) 5.00 (s, 1H), 6.76-7.77 (m, 12H). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:P(OC(C)C)(OC(C)C)[O-], amount is: 0.0 ;m1_m2_m3:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m3:C=O, amount is: 0.0 ;m4:C=O, 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:OCP(OC(C)C)(OC(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 33.2 g (0.20 mol) of diisopropyl phosphite, 2.8 mL (0.02 mol) of triethylamine, and 6.0 g (0.20 mol) of paraformaldehyde, was immersed in a 100° C. oil bath and then heated between 100°-120° C. for 45 minutes under nitrogen. An exotherm occurred within 10 minutes, and all of the paraformaldehyde dissolved rapidly. The triethylamine was removed at reduced pressure, and the residue was bulb-to-bulb distilled in four portions to provide a total of 35.17 g (90%) of the title compound as a colorless oil. |
Here is a chemical reaction formula: Reactants are m4:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE;m1_m2_m3_m5:C(C)(=O)OC(C)=O, amount is: 0.0 ;m1_m2_m3_m5:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 ;m1_m2_m3_m5:COC1=CC=2CC[C@H]3[C@@H]4C=C(C([C@@]4(C)CC[C@@H]3C2C=C1)=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(C)(=O)OC(=C)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)OC=1[C@]2(C)C(=CC1C)[C@@H]1CCC=3C=C(C=CC3[C@H]1CC2)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Acetic anhydride (80 ml) and p-toluene sulfonic acid (6 g) are added to a suspension of 3-methoxy-16-methylestra-1,3,5(10),15-tetraen-17-one (1) (DE-OS 3,023,568 (1982)) (20 g; 67.7 mmol) in isopropenyl acetate (400 ml). The reaction mixture is stirred for about 20 hours at 100° C. After cooling it is poured on ice water and neutralized by addition of small portions of sodium bicarbonate. It is extracted three times with benzene, the combined organic phases are washed with water, dried on magnesium sulfate and concentrated by evaporation in a vacuum. The resulting brown residue (23.5 g) is chromatographed on silica gel with a mixture of ethyl acetate/benzene (1:49). The yellowish crystalline productis further purified by recrystallization of ethyl acetate/methanol. 19.8 g (87%) of colorless 14,16-diene-17-acetate (2) is obtained. |
Here is a chemical reaction formula: Reactants are m3_m1:C(C1=CC=CC=C1)OC1=CC=2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3C2C=C1)OCCOC(CCCC1=CC=C(C=C1)N(CCCl)CCCl)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m1:O1CCOCC1, amount is: 0.0 ;m4:O1CCOCC1, amount is: 0.0 ,Catalysts are m2:[Pd], amount is: 0.0 .Products are 0:OC1=CC=2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3C2C=C1)OCCOC(CCCC1=CC=C(C=C1)N(CCCl)CCCl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 10% palladium on carbon (320.7 mg) was placed into an eggplant type flask (100 ml), followed by dropwise addition of 1,4-dioxane (15 ml) at 0° C. To this mixture was added a 1,4-dioxane (15 ml) solution of 1-[3-benzyloxy-1,3,5(10)-estratriene-17β-oxy]-2-[4-[p-[bis(2-chloroethyl)amino]phenyl]-butyryloxy]ethane (I-5) dropwise at 0° C. The mixture was heated to room temperature and stirred under hydrogen gas for one hour. The reaction mixture was filtered through filter paper while washing with 1,4-dioxane, and the filtrate was concentrated under reduced pressure to produce an oily substance (0.27 g). It was purified by silica gel chromatography (hexane/ethyl acetate=3:1) to obtain 1-[3-hydroxy-1,3,5(10)-estratriene-17β-oxy]-2-[4-[p-[bis(2-chloroethyl)amino]phenyl]butyryloxy]ethane (0.26 g) (Rf: 0.25, hexane/ethyl acetate=3:1) as oily substance. |
Here is a chemical reaction formula: Reactants are m3:BrC=1C=C(C=C2C=CC(=NC12)Cl)C, amount is: 0.0 ;m2:FC(CO)(F)F, amount is: 0.0 ;m4_m7:C(C)(=O)OCC, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m7:O, amount is: 0.0 MOLE;m6_m0:CCCCCC.C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C=C(C=C2C=CC(=NC12)OCC(F)(F)F)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 0.8 g of 60% sodium hydride (oil dispersion) stirring in 20 ml of tetrahydrofuran at room temperature, 2.5 ml (34.3 mmol) of 2,2,2-trifluoroethanol was added dropwise. An exotherm occurred and to theresulting solution 1.7 g (6.7 mmol) of 8-bromo-2-chloro-6-methyl-quinoline was added followed by heating at reflux for 7 h. Ethyl acetate (200 ml) and excess water was added and the organic layer separated and washed withwater and brine, dried over magnesium sulfate, and evaporated in vacuo to give an oil. Silica gel column chromatography (20:1 followed by 10:1 hexane/ethyl acetate) afforded 1.9 g of 8-bromo-6-methyl-2-(2,2,2-trifluoroethoxy)quinoline, m.p. 61°-62° C. |
Here is a chemical reaction formula: Reactants are m3_m4:C(C)(=O)OCC, amount is: 0.0 ;m3_m4:O, amount is: 0.0 MOLE;m1_m2_m6:BrC=1C=C(C=C2C=CC(=NC12)OCC(F)(F)F)C, amount is: 0.0 ;m1_m2_m6:FC(C=1C=C(C=CC1)[Sn](C)(C)C)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C1(=CC=CC=C1)C, amount is: 0.0 ;m7_m0:CCCCCC.C(C)(=O)OCC, amount is: 0.0 MOLE,Catalysts are m1_m2_m6: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.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.[Pd], amount is: 0.0 .Products are 0:CC=1C=C2C=CC(=NC2=C(C1)C1=CC(=CC=C1)C(F)(F)F)OCC(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1.5 g (6.2 mmol) of 8-bromo-6-methyl-2-(2,2,2-trifluoroethoxy)quinoline, 2.3 g of crude 3-(trifluoromethyl)phenyltrimethylstannane (Example 1), and 0.2 g of tetrakis(triphenylphosphine)palladium(O) was heated in 30 ml of toluene atreflux with stirring for 3 hours. Ethyl acetate (200 ml) and excess water was added. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo to give an oil. Silica gel column chromatography (20:1 followed by 10:1 hexane/ethyl acetate) afforded 0.7 g of product, isolated as an oil. NMR(CDCl3): ppm 2.55 (s, 3H), 4.71 (q, 2H), 7.15 (d, 1H), 7.5-8.15 (m, 7H). |
Here is a chemical reaction formula: Reactants are m1_m3_m4:BrC1=C(N)C(=CC(=C1)C)[N+](=O)[O-], amount is: 0.0 ;m2_m5:N#CN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4:C(C)(=O)O, amount is: 0.0 ;m1_m3_m4:Cl, amount is: 0.0 ;m2_m5:Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC=1N=[N+](C2=C(N1)C(=CC(=C2)C)Br)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 13.0 g (56.3 mmol) of 2-bromo-4-methyl-6-nitroaniline stirring in a mixture of 25 ml glacial acetic acid and 5 ml of concentrated hydrochloricacid at 80° C., 29.0 g (690.5 mmol) of cyanamide and 25 ml of concentrated hydrochloric acid were added simultaneously, separately, and very slowly. At one point during the addition, a vigorous exotherm occurred and the external heat immediately removed. After the addition, the reaction was heated at reflux for 15 minutes. On cooling to about 50° C., 100 ml of 25% aqueous sodium hydroxide were added dropwise and the mixture heated at reflux 15 minutes. The reaction was cooled to room temperature, the insoluble orange solid filtered and washed with water followed by ethyl acetate to afford 7.4 g of yellow 3-amino-5-bromo-7-methyl-1,2,4-benzotriazine-1-oxide after drying. |
Here is a chemical reaction formula: Reactants are m1_m5_m2:[H-].[Na+], amount is: 0.0 ;m1_m5_m2:FC(CO)(F)F, amount is: 0.0 MOLE;m3:BrC1=CC(=CC2=C1N=C(N=[N+]2[O-])Cl)C, amount is: 0.0 ;m4_m6:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:O1CCCC1, amount is: 0.0 ;m4_m6:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:BrC1=CC(=CC2=C1N=C(N=[N+]2[O-])OCC(F)(F)F)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 0.5 g of 60% sodium hydride stirring in 30 ml of tetrahydrofuran, 3.0 mlof 2,2,2-trifluoroethanol was added dropwise at ambient temperature. A solution resulted and 2.0 g (7.29 mmol) of the above 5-bromo-3-chloro-7-methyl-1,2,4-benzotriazine-1-oxide was added and at ambient temperature and the mixture stirred 2 h. Ethyl acetate (200 ml) and excess water were added and the separated organic extract washed with water, brine, and dried over magnesium sulfate. The solvent was removed invacuo, hexane added to the residue, and the suspended yellow s 61id filtered and dried to afford 1.7 g of 5-bromo-7-methyl-3-(2,2,2-trifluoroethoxy) -1,2,4-benzotriazine-1-oxide, m.p. 127°-128° C. |
Here is a chemical reaction formula: Reactants are m1_m2:C1(CC1)C(O)C=1SC=CC1, amount is: 0.0 ;m1_m2:Br, 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:BrCC/C=C/C=1SC=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 225 g (1.46 mol) of cyclopropyl-2-thienylcarbinol were added dropwise to 972 ml of 48% strength hydrobromic acid at from 5° to 10° C.in the course of 1 hour. After 2 hours at room temperature, the organic phase was separated off and the aqueous solution was extracted with three times 300 ml of dichloromethane. The combined organic phases were washed neutral with dilute sodium hydroxide solution and water, dried over magnesium sulfate and evaporated down under reduced pressure. 322 g (94% corrected) of crude bromide (GC: 92%) were obtained. 250 MHz-1H-NMR (in CDCl3): δ [ppm]=2.65-2.80 (m, 2H), 3.46 (t, 2H), 5.90-6.10 (m, 1H), 6.61 (d, 1H), 6.80-7.00 (m, 2H), 7.14 (d, 1H). |
Here is a chemical reaction formula: Reactants are m1_m2_m4:ClCCC(C(=O)OCC)(C)C, amount is: 0.0 ;m1_m2_m4:[S-]C#N.[K+], amount is: 0.0 ;m3:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C(=O)OCC)(CCSC#N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 22.1 g of ethyl 4-chloro-2,2-dimethylbutyrate and 14.5 g of potassium thiocyanate were dissolved in 100 ml of dimethylformamide, followed by stirring at 100° C. for 7 hours. The reaction mixture was added to 500 ml of water and extracted with ethyl ether. After the extract was washed with water and dried over MgSO4, the solvent was distilled off. The residue was distilled under reduced pressure to yield 16.4 g of the title compound in the form of a colorless oily substance. |
Here is a chemical reaction formula: Reactants are m2_m5:NS(=O)(=O)CCC(C(=O)OCC)(C)C, amount is: 0.0 ;m1_m4:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 0.0 ;m3:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m5:O1CCCC1, amount is: 0.0 ;m6:O1CCCC1, amount is: 0.0 MOLE;m1_m4:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OCC(CCS(=O)(=O)N)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 0.35 g of lithium aluminum hydride in 30 ml of tetrahydrofuran being stirred under ice cooling conditions, a solution of 1.5 g of ethyl 4-aminosulfonyl-2,2-dimethylbutyrate in 8 ml of tetrahydrofuran was added dropwise, followed by stirring at 0° C. for 30 minutes and then at room temperature (15° to 20° C.) for 30 minutes. To the reaction mixture was added aqueous tetrahydrofuran to decompose excess lithium aluminum hydride, followed by neutralization with 2 N hydrochloric acid and extraction with ethyl acetate. After the extract was washed with water and dried over MgSO4, the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with hexane:ethyl acetate (1:1) to yield 0.94 g of the title compound. |
Here is a chemical reaction formula: Reactants are m2:BrCCCCBr, amount is: 0.0 MOLE;m1:C(C(C)C)(=O)OCC, 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:BrCCCCC(C(=O)OCC)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using ethyl isobutyrate and 1,4-dibromobutane, the title compound was produced in the same manner as in Reference Example 6. |
Here is a chemical reaction formula: Reactants are m2:BrCCCl, amount is: 0.0 MOLE;m1:C(C)C(C(=O)OCC)CC, 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:ClCCC(C(=O)OCC)(CC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using ethyl 2-ethylbutyrate and 1-bromo-2-chloroethane, the title compound was produced in the same manner as in Reference Example 6. |
Here is a chemical reaction formula: Reactants are m2:BrCCCBr, amount is: 0.0 MOLE;m1:C(C)C(C(=O)OCC)CC, 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:BrCCCC(C(=O)OCC)(CC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using ethyl 2-ethylbutyrate and 1,3-dibromopropane, the title compound was produced in the same manner as in Reference Example 6. |
Here is a chemical reaction formula: Reactants are m2:BrCCCCBr, amount is: 0.0 MOLE;m1:C(C)C(C(=O)OCC)CC, 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:BrCCCCC(C(=O)OCC)(CC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using ethyl 2-ethylbutyrate and 1,4-dibromobutane, the title compound was produced in the same manner as in Reference Example 6. |
Here is a chemical reaction formula: Reactants are m1:BrCCCCC(C(=O)OCC)(C)C, amount is: 0.0 MOLE;m2:[S-]C#N.[K+], 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:CC(C(=O)OCC)(CCCCSC#N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using ethyl 6-bromo-2,2-dimethylhexanate as obtained in Reference Example 7and potassium thiocyanate, the title compound was produced in the same manner as in Reference Example 11. |
Here is a chemical reaction formula: Reactants are m2:[S-]C#N.[K+], amount is: 0.0 MOLE;m1:ClCCC(C(=O)OCC)(CC)CC, 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(C)C(C(=O)OCC)(CCSC#N)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using ethyl 4-chloro-2,2-diethylbutyrate as obtained in Reference Example 8and potassium thiocyanate, the title compound was produced in the same manner as in Reference Example 11. |
Here is a chemical reaction formula: Reactants are m2:[S-]C#N.[K+], amount is: 0.0 MOLE;m1:BrCCCCC(C(=O)OCC)(CC)CC, 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(C)C(C(=O)OCC)(CCCCSC#N)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using ethyl 6-bromo-2,2-diethylhexanate as obtained in Reference Example 10and potassium thiocyanate, the title compound was produced in the same manner as in Reference Example 11. |
Here is a chemical reaction formula: Reactants are m1:C(C)(=O)OCCCS(=O)(=O)Cl, amount is: 0.0 MOLE;m2:CNC, 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:OCCCS(=O)(=O)N(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 3-acetoxy-1-propanesulfonylchloride and dimethylamine, substantially the same reaction was conducted as in reference example 47 and 48 to produce the title compound. |
Here is a chemical reaction formula: Reactants are m3:ClC=1C(=C(C=2N(N1)C=CN2)C)C, amount is: 0.0 ;m2:OCC(CS(=O)(=O)N)(C)C, amount is: 0.0 ;m1:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C(C=2N(N=C1OCC(CS(N)(=O)=O)(C)C)C=CN2)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.59 g of 60% oily sodium hydride was suspended in 21 ml of dimethylformamide. To this suspension, 1.18 g of 3-hydroxy-2,2-dimethyl-1-propanesulfonamide was added, followed by stirring at room temperature (15° to 20° C.) under reduced pressure for 1 hour. To this mixture was added 1.28 g of 6-chloro-7,8-dimethylimidazo[1,2-b]pyridazine, followed by stirring at 60° C. for 40 minutes. After dimethylformamide was distilled off under reduced pressure, ice water was added to the residue, which was subsequently adjusted to pH 6 by the addition of 5 N hydrochloric acid andthen extracted with ethyl acetate-tetrahydrofuran (2:1). The extract was washed with 20 ml of saturated saline and then dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with dichloromethane-ethyl acetate-methanol (10:10:1). The fraction containing the desired product was concentrated and recrystallized from ethanol to yield 0.866 g of the title compound. |
Here is a chemical reaction formula: Reactants are m3:C(C)OCC, amount is: 0.0 MOLE;m1:CC1=C(C=2N(N=C1OCC(CS(N)(=O)=O)(C)C)C=CN2)C, amount is: 0.0 ;m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.CC1=C(C=2N(N=C1OCC(CS(N)(=O)=O)(C)C)C=CN2)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.421 g of 7,8-dimethyl-6-(2,2-dimethyl-3-sulfamoyl-1-propoxy)imidazo[1,2-b]pyridazine was suspended in 20 ml of ethanol. To this suspension, 1.65 ml of 1 N hydrochloric acid was added. After the resulting solution was concentratedunder reduced pressure, ethyl ether was added to the residue to cause crystallization, to yield 0.45 g of the title compound. |
Here is a chemical reaction formula: Reactants are m3:C(C)O.C(C)OCC, amount is: 0.0 MOLE;m1:CC(COC=1C(=CC=2N(N1)C=CN2)C)(CS(N)(=O)=O)C, amount is: 0.0 ;m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.CC(COC=1C(=CC=2N(N1)C=CN2)C)(CS(N)(=O)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.503 g of 6-(2,2-dimethyl-3-sulfamoyl-1-propoxy)-7-methylimidazo[1,2-b]pyridazine was suspended in 15 ml of ethanol. To this suspension, 1.8 ml of 1 N hydrochloric acid was added. After the resulting solution was concentratedunder reduced pressure, ethanol-ethyl ether (4:1) was added to the residue to cause crystallization to yield 0.533 g of the title compound. |
Here is a chemical reaction formula: Reactants are m1:[H-].[Na+], amount is: 0.0 ;m3:ClC1=NN2C(C=3CCCCC13)=NC=C2, amount is: 0.0 ;m2:OCC(CS(=O)(=O)N)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(COC1=NN2C(C=3CCCCC13)=NC=C2)(CS(N)(=O)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.59 g of 60% oily sodium hydride was suspended in 20 ml of dimethylformamide. To this suspension, 1.18 g of 3-hydroxy-2,2-dimethyl-1-propanesulfonamide was added, followed by stirring at room temperature (15° to 20° C.) under reduced pressure for 30 minutes. To this mixture was added 1.35 g of 6-chloro-7,8,9,10-tetrahydroimidazo[2,1-a]phthalazine, followed by stirring at 60° C. for 1.5 hours. After dimethylformamide was distilled off under reduced pressure, ice water was added to the residue, which was subsequently adjusted to pH 6 by the addition of 5 N hydrochloric acid and then extracted with ethyl acetate-tetrahydrofuran (2:1). The extract was washed with 20 ml of saturated saline and then dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with dichloromethane-ethyl acetate-methanol (20:20:1). The fraction containing the desired product was concentrated, and ethyl ether was added to separate a crystal, which was collected by filtration, to yield 0.66 g of the title compound. |
Here is a chemical reaction formula: Reactants are m3:ClC1=NN2C(C3=CC=CC=C13)=NC=C2, amount is: 0.0 ;m1:[H-].[Na+], amount is: 0.0 ;m2:OCC(CS(=O)(=O)N)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(COC1=NN2C(C3=CC=CC=C13)=NC=C2)(CS(N)(=O)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.293 g of 60% oily sodium hydride was suspended in 10 ml of dimethylformamide. To this suspension, 0.577 g of 3-hydroxy-2,2-dimethyl -1-propanesulfonamide was added, followed by stirring at room temperature (15° to 20° C.) under reduced pressure for 30 minutes. To this mixture was added 0.703 g of 6-chloroimidazo[2,1-a]phthalazine, followed by stirring at room temperature for 3 hours. After dimethylformamide was distilled off under reduced pressure, ice water was added to the residue, which was subsequently adjusted to pH 5.0 by the addition of 5 N hydrochloric acid and then extracted with ethyl acetate-tetrahydrofuran (1:1). The extract was washed with 20 ml of saturated saline and then dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with dichloromethane-ethyl acetate-methanol (20:20:1). The fraction containing the desired product was concentrated and ethyl ether was added to separate a crystal, which was collected by filtration, to yield 0.769 g of the title compound. |
Here is a chemical reaction formula: Reactants are m1:ClC=1C(=CC=2N(N1)C=CN2)C, amount is: 0.0 ;m2:OCC(CCS(=O)(=O)N)(C)C, 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:CC(COC=1C(=CC=2N(N1)C=CN2)C)(CCS(N)(=O)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 0.84 g of 6-chloro-7-methylimidazo[1,2-b]pyridazine and 0.91 g of 4-hydroxy-3,3-dimethyl-1-butanesulfonamide, 0.41 g of title compound was obtained in the same manner as in Example 3. |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 MOLE;m3:ClC=1C(=CC=2N(N1)C=CN2)C, amount is: 0.0 ;m1_m5_m2:CN(C)C=NS(=O)(=O)CC(CO)(CC)CC, amount is: 0.0 ;m1_m5_m2:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)C(COC=1C(=CC=2N(N1)C=CN2)C)(CS(N)(=O)=O)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1.38 g of 3-(N,N-dimethylaminomethyl-ene)aminosulfonyl -2,2-diethyl-1-propanol in 30 ml of tetrahydrofuran, 0.23 g of 60% oily sodium hydride was added, followed by stirring at room temperature for 1 hour. To the reaction mixture, 0.74 g of 6-chloro-7-methylimidazo [1,2-b]pyridazine was added, followed by refluxing under heating conditions for 1 hour. After cooling, the reaction mixture was neutralizedwith 1 N hydrochloric acid and extracted with ethyl acetate-tetrahydrofuran(1:1). After the extract was washed with water and dried over MgSO4, the solvent was distilled off under reduced pressure. To the residue was added 14 ml of 6 N hydrochloric acid, followed by stirring at 110° C. for 30 minutes. After cooling, the mixture was concentrated under reduced pressure, and the residue adjusted to a pH of 7 by addition of aqueous solution of sodium hydrogen carbonate and then extracted with ethyl acetate. After saline washing, the extract was dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue subjected to column chromatography using 100 g of silica gel, eluted with chloroform-methanol (5:1), and crystallized from a mixed solvent of methanol and ethyl acetate, to yield 1.19 g of the title compound. |
Here is a chemical reaction formula: Reactants are m2:CN(C)C=NS(=O)(=O)CCCC(CO)(CC)CC, amount is: 0.0 ;m1:ClC=1C(=CC=2N(N1)C=CN2)C, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)C(COC=1C(=CC=2N(N1)C=CN2)C)(CCCS(N)(=O)=O)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 0.8 g of 6-chloro-7-methylimidazo[1,2-b]pyridazine and 1.52 g of 5-(N,N-dimethylaminomethylene)aminosulfonyl-2,2-diethyl-1-pentanol, 0.84 gof the title compound was obtained in the same manner as in Example 14. |
Here is a chemical reaction formula: Reactants are m2:CN(C)C=NS(=O)(=O)CC(CO)C(C)C, amount is: 0.0 ;m1:ClC=1C(=CC=2N(N1)C=CN2)C, 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(C)(C)C(COC=1C(=CC=2N(N1)C=CN2)C)CS(N)(=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 0.8 g of 6-chloro-7-methylimidazo[1,2-b]pyridazine and 1.29 g of 3-(N,N-dimethylaminomethylene)aminosulfonyl-2-isopropyl-1-propanol, 1.37 gof the title compound was obtained in the same manner as in Examples 14 and |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m2:CN1CCN(CC1)S(=O)(=O)CCCO, amount is: 0.0 ;m3:ClC=1C(=CC=2N(N1)C=CN2)C, amount is: 0.0 ;m1:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O1CCCC1.CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=CC=2N(N=C1OCCCS(=O)(=O)N1CCN(CC1)C)C=CN2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In 20 ml of tetrahydrofuran-dimethylformamide (3:1) was suspended 110 mg of60% sodium hydride in oil followed by addition of 611 mg of 3-(1-methyl-4-piperazinylsulfonyl)-1-propanol and the mixture was stirred under nitrogen at room temperature for 30 minutes and at 50° C. for30 minutes. Then, 420 mg of 6-chloro-7-methylimidazo[1,2-b]pyridazine was added and the mixture was further stirred at 50° C. for 1 hour and at 70° C. for 1 hour. Following addition of 100 ml of iced water, the reaction mixture was extracted with ethylacetate (100 ml ). The extract was washed with 50 ml of saturated saline and dried over anhydrousmagnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was subjected to silica gel column chromatography, elution being carried out with dichloromethanemethanol (50:3). The fraction containing the desired product were pooled and concentrated. The residue was recrystallized dichloromethane-isopropyl ether to obtain 447 mg of the title compound. |
Here is a chemical reaction formula: Reactants are m2:O=[O+][O-], amount is: 0.0 MOLE;m1_m3_m4:O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)NCCCC1=CC=CC=C1)CCC=C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4:C(Cl)Cl, amount is: 0.0 ;m1_m3_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)NCCCC1=CC=CC=C1)CCC=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl-5-hexenylamine (1.2 g, 3.19 mmol) in methylene chloride (40 mL) and methanol (4 mL) and cool to -78° C. under a nitrogen atmosphere. Treat with ozone until a blue color persists, degas with nitrogen for 20 minutes and add pyridine (0.2 mL). Quench with dimethylsulfide (4 mL) and stir overnight at room temperature. Dilute with methylene chloride (75 mL) and wash with 5% sulfuric acid (40 mL) and brine (40 mL). Dry (Na2SO4), evaporate the solvent in vacuo and purify by chromatography (hexane/ethyl acetate) to give 2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl-5-oxo-pentylamine as a white solid (972 mg, 80%). |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:C1C(CC2=CC=CC=C12)C(=O)O, amount is: 0.0 ;m1_m4_m2_m3:COC(C)(C)OC, amount is: 0.0 ;m1_m4_m2_m3:S(O)(O)(=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(OC)C1CC2=CC=CC=C2C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2-indancarboxylic acid (3.82 g, 23.5 mmol) in methanol (60 mL) andtreat with dimethoxypropane (5.8 mL, 47 mmol) and sulfuric acid (0.8 mL). Stir at room temperature for 6 days. Evaporate the solvent in vacuo, dilute with methylene chloride (75 mL) and wash with saturated sodium hydrogen carbonate (35 mL). Extract the aqueous phase with methylene chloride (30 mL), wash combined organics with brine (30 mL) and dry (Na2SO4). Evaporate the solvent in vacuo and pass through a plug of silica gel to give 2-(carbomethoxy)indan as a yellow oil (3.98 g, 96%). |
Here is a chemical reaction formula: Reactants are m1_m3_m4_m5:C(=O)(OC)C1(CC2=CC=CC=C2C1)SCC1=CC=C(C=C1)OC, amount is: 0.0 ;m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4_m5:C(C)O, amount is: 0.0 ;m1_m3_m4_m5:O, amount is: 0.0 ;m1_m3_m4_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1(CC2=CC=CC=C2C1)SCC1=CC=C(C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2-(carbomethoxy)-2-(4-methoxybenzylthio)indan (2.20 g, 3.55 mmol) in 95% ethanol (25 mL), water (12 mL) and tetrahydrofuran (15 mL). Treat with potassium hydroxide (1.3 g, 23 mmol) and stir at room temperature for1 hour. Filter and evaporate the solvent in vacuo. Partition between water (125 mL) and ether (75 mL). Separate the aqueous phase and acidify with cold concentrated hydrochloric acid. Extract with methylene chloride (75 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify bysilica gel chromatography (2:1 hexane/ethyl acetate) to give 2-carboxy-2-(4-methoxybenzylthio)indan as a yellow solid (0.48 g, 43%). |
Here is a chemical reaction formula: Reactants are m3:BrCC=1C(=CC=CC1)CBr, amount is: 0.0 ;m4:[H-].[Na+], amount is: 50.0 MILLIMOLE;m1_m5:C(CC(=O)OCC)(=O)OCC, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(OCC)C1(CC2=CC=CC=C2C1)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve diethyl malonate (7.6 mL, 50 mmol) in anhydrous tetrahydrofuran (500 mL) and place under an argon atmosphere. Cool to 5° C., add sodium hydride (1.2 g, 50 mmol) and stir briefly until homogeneous. Add α,α'-dibromo-o-xylene (13.2 g, 50 mmol) and stir an additional15 minutes. Add additional sodium hydride (1 .2 g, 50 mmol) and stir for 16hours while warming to room temperature. Filter, evaporate the solvent in vacuo and purify by silica gel chromatography (1:1 methylene chloride/hexane) to give 2,2-dicarboethoxyindan (9.64 g, 74%). |
Here is a chemical reaction formula: Reactants are m1_m3:C(=O)(OCC)C1(CC2=CC=CC=C2C1)C(=O)OCC, amount is: 0.0 ;m2:[OH-].[Li+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1CC2=CC=CC=C2C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2,2-dicarboethoxy-indan (5.67 g, 21.7 mmol) in ethanol (150 mL). Add 1N lithium hydroxide (50 mL) and stir overnight at room temperature. Reflux for 1 hour and concentrate the solution in vacuo. Partition betweenethyl acetate and 6N hydrochloric acid. Separate the organic phase and washwith brine. Dry (MgSO4) and evaporate the solvent in vacuo to give an off-white solid. Distill (120°-160° C. @0.2-0.5 mmHg) to give 2-carboxy-indan (2.5 g, 71%). |
Here is a chemical reaction formula: Reactants are m1_m2:C(=O)(O)C1CC2=CC=CC=C2C1, amount is: 0.0 ;m1_m2:CO, 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(=O)(OC)C1CC2=CC=CC=C2C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2-carboxy-indan (2.5 g, 15.4 mmol) in methanol and cool to 0° C. Saturate with hydrochloride gas then add 2,2-dimethoxypropane(2-3 mL). Stir overnight then evaporate the solvent in vacuo. Purify by silica gel chromatography (2:1 methylene chloride/hexane) to give 2-carbomethoxy-indan as a water white oil. (2.04 g, 75%). |
Here is a chemical reaction formula: Reactants are m1_m3:C(=O)(OC)C1(CC2=CC=CC=C2C1)CSC(C)(C)C, amount is: 0.0 ;m2:[OH-].[Li+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1(CC2=CC=CC=C2C1)CSC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2-carbomethoxy-2-(t-butyl)thiomethyl-indan (557 mg, 2.0 mmol) in methanol (15 mL) and add 1N lithium hydroxide (3.5 mL). Warm briefly to effect solution then stir at room temperature under an argon atmosphere for 1 hour. Reflux for 6 hours, concentrate in vacuo to a volume of 3 mL and dilute to a volume of 15 mL with water. Wash with methylene chloride and acidify and aqueous phase with excess 2N hydrochloric acid. After 5 minutes, collect the resulting white precipitate by filtration and dry to give 2-carboxy-2-(t-butyl)thiomethyl-indan (506 mg, 96%); mp 158°-163° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m4_m5:C(=O)(OC)C1(CCCC1)SCC1=CC=C(C=C1)OC, amount is: 3.299999952316284 MILLIMOLE;m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4_m5:C(C)O, amount is: 0.0 ;m1_m3_m4_m5:O, amount is: 0.0 ;m1_m3_m4_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1(CCCC1)SCC1=CC=C(C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 1-(carbomethoxy)-1-(4-methoxylbenzylthio)cyclopentane (3.3 mmol) in 95% ethanol (18 mL) , water (9 mL), and tetrahydrofuran (10 mL). Treat with potassium hydroxide (0.91 g, 16 mmol). Stir at room temperature for 2hours and evaporate the solvent in vacuo. Partition between water (50 mL) and ethyl ether (30 mL). Acidify the aqueous phase with cold concentrated hydrochloric acid and extract with methylene chloride (50 mL). Dry (MgSO4) and evaporate the solvent in vacuo to give 1-(carboxy)-1-(4-methoxybenzylthio)cyclopentane as a pale yellow oil (483 mg, 72%). |
Here is a chemical reaction formula: Reactants are m1_m3_m4:C(=O)(OCC)C1CC=2C(=COC2)C1, amount is: 0.0 ;m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4:C(C)O, amount is: 0.0 ;m1_m3_m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1CC=2C(=COC2)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 5-(carboethoxy)-2,4,5,6-tetrahydrocyclopenta[c]furan (6.2 g, 34.1 mmol) in ethanol (95%, 150 mL) and water (75 mL). Add potassium hydroxide (9.5 g, 0.17 mol) and stir at room temperature for 1 hour. Partition between water (150 mL) and ethyl ether (2×150 mL). Acidify the aqueous phase with hydrochloric acid to pH 1. Extract with methylene chloride (2×150 mL), dry (Na2SO4) and evaporate the solvent in vacuo to give 5-(carboxy)-2,4,5,6-tetrahydrocyclopenta[c]furan. |
Here is a chemical reaction formula: Reactants are m2_m3:COC(C)(C)OC, amount is: 47.0 MILLIMOLE;m2_m3:S(O)(O)(=O)=O, amount is: 0.0 ;m1_m4:C(=O)(O)C1CC=2C(=COC2)C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(OC)C1CC=2C(=COC2)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 5-(carboxy)-2,4,5,6-tetrahydro-cyclopenta[c]furan (3.6 g, 23.5 mmol) in methanol (60 mL) and treat with dimethoxypropane (5 .8 mL, 47 mmol) and sulfuric acid (0.8 mL). Stir at room temperature for 1 day. Evaporate the solvent in vacuo, dilute with methylene chloride (75 mL) andwash with saturated sodium hydrogen carbonate (35 mL). Extract the aqueous phase with methylene chloride (30 mL), wash combined organics with brine (30 mL) and dry (Na2SO4). Evaporate the solvent in vacuo and pass through a plug of silica gel to give 5-(carbomethoxy)-2,4,5,6-tetrahydrocyclopenta[c]furan. |
Here is a chemical reaction formula: Reactants are m2:[OH-].[K+], amount is: 23.0 MILLIMOLE;m1_m3_m4_m5:C(=O)(OC)C1(CC=2C(=COC2)C1)SCC1=CC=C(C=C1)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4_m5:C(C)O, amount is: 0.0 ;m1_m3_m4_m5:O, amount is: 0.0 ;m1_m3_m4_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1(CC=2C(=COC2)C1)SCC1=CC=C(C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 5-(carbomethoxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydro-cyclopenta[c]furan (1.08 g, 3.55 mmol) in 95% ethanol (25 mL), water (12 mL) and tetrahydrofuran (15 mL). Treat with potassium hydroxide (lo3 g, 23 mmol) and stir at room temperature for 1 hour. Filter and evaporate the solvent in vacuo. Partition between water (125 mL) and ether (75 mL). Separate theaqueous phase and acidify with cold concentrated hydrochloric acid. Extractwith methylene chloride (75 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give 5-(carboxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydrocyclopenta[c]furan. |