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Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=CC=C(C=C1)C=1C=CC(NN1)=O, amount is: 0.0 ;m1_m3_m2:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1C=CC(NN1)=S, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3.0 g of 6-(4-chlorophenyl)-pyridazinone, 50 ml of dry pyridine and 3.2 g of phosphorus pentasulfide was refluxed for 1 hour, evaporated to dryness and extracted with 200 ml of ether. The ether extract was washed with water (3×100 ml), brine (100 ml), dried over magnesium sulfate and evaporated to yield 3.0 g of 6-(4-chlorophenyl)-pyridazinthione as a yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=CC=C(C(=O)NN)C=C1, amount is: 0.0 ;m1_m3_m2:ClCC(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:O1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCC(=O)NNC(C1=CC=C(C=C1)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of p-chlorobenzoic hydrazide (11.2 g) in dioxane (100 ml) was added chloroacetyl chloride (6 ml). The resulting mixture was refluxed for three hours cooled to room temperature and filtered. The resulting solid was washed with ethyl ether and dried to yield N'-chloroacetyl-4-chlorobenzoic hydrazide as white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:BrCC(=O)C1=CC=C(C=C1)Cl, amount is: 0.0 ;m1_m2_m3:COC(=S)NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C1=NNC(SC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-bromo-p-chloroacetophenone (9.16 g), methoxythiocarbonylhydrazine (13.0 g) and acetonitrile (75 ml) was refluxed overnight and then cooled and filtered. The light yellow solid was washed with hexane and dried yielding 5-(4-chlorophenyl)-3H,6H-1,3,4-thiadiazin-2-one (4.3 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=CC=C(C=O)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(CCC(=O)C)(=O)O, amount is: 0.0 ;m1_m2_m3_m4:N1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=CC(=O)CCC(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a dry 250 ml flask equipped with a magnetic stirrer, Dean-Stark trap, and reflux condenser was charged 15 g of 4-chlorobenzaldehyde, 12.4 g levulenic acid, 5.7 ml of piperidine, and 100 ml of toluene. The reaction was refluxed for 3 hours, after which no water was observed to azeotrope from the solution. The reaction was cooled and stripped to yield a reddish-brown liquid which was triturated with hexane to yield 11.2 g of product as a yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:[N+](=O)([O-])C=1C(=C(C(=O)[O-])C=CC1OC)C, amount is: 0.0 ;m1_m3_m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a 500 ml erlenmeyer flask with magnetic stirrer was charged 10.3 g of 3-nitro-4-methoxy-methylbenzoate, 400 ml tetrahydrofuran, and 3.2 g of 86% potassium hydroxide. The reaction was stirred for 12 hours at ambient temperature, after which the resulting solid was collected by vacuum filtration and washed with 2×100 ml of ethyl ether. The solid was dissolved in 200 ml of water and acidified to pH 4 with 6N hydrochloric acid. The resulting precipitate was collected by vacuum filtration, washed with 200 ml water, and dried overnight in vacuo at 30° C. Isolated 7.4 g of product as a white solid. |
Here is a chemical reaction formula: Reactants are m3:C([C@@H]1CO1)OS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-], amount is: 0.0 ;m1_m2_m4:C(C1=CC=CC=C1)OC1=C(C=CC=C1)O, amount is: 0.0 ;m1_m2_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C([C@H]1CO1)C=1C(=C(C=CC1)O)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-benzyloxyphenol (900 mg, 4.5 mMol) and potassium carbonate (1.87 g, 13.5 mMol) in acetone (45 ml) was heated under reflux for 15 mins. (S)-Glycidyl-3-nitrobenzenesulphonate (1.0 g, 4.5 mMol) was added and the reaction mixture was heated under reflux for 23 hours. After cooling, the reaction mixture was filtered and the solvent was evaporated. The residue was partitioned between ethyl acetate and water. The organic fractions were combined, washed with water and brine, dried and evaporated to give the title compound as an oil. |
Here is a chemical reaction formula: Reactants are m3:C([C@@H]1CO1)OS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-], amount is: 0.0 ;m1_m2_m4:C(C1=CC=CC=C1)OC=1C=C(C=CC1)O, amount is: 0.0 ;m1_m2_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C([C@H]1CO1)C1=C(C=CC=C1OCC1=CC=CC=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3-benzyloxyphenol (900 mg, 4.5 mMol) and potassium carbonate (1.87 g, 13.5 mMol) in acetone (45 ml) was heated under reflux for 15 mins. (S)-Glycidyl-3-nitrobenzenesulphonate (1.0 g, 4.5 mMol) was added and the reaction mixture was heated under reflux for 23 hours. After cooling the reaction mixture was filtered and the solvent was evaporated. The residue was partitioned between ethyl acetate and water. The organic fractions were combined, washed with water and brine, dried and evaporated to give the title compound as an oil. |
Here is a chemical reaction formula: Reactants are m3:C([C@@H]1CO1)OS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-], amount is: 0.0 ;m1_m2_m4:C(C1=CC=CC=C1)OC1=CC=C(C=C1)O, amount is: 0.0 ;m1_m2_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C([C@H]1CO1)C1=C(C=CC(=C1)OCC1=CC=CC=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-benzyloxyphenol (2.0 g, 10 mMol) and potassium carbonate (4.14 g, 30 mMol) in acetone (50 ml) was heated under reflux for 15 mins. (S)-Glycidyl-3-nitrobenzenesulphonate (2.23 g, 10 mMol) was added and the reaction mixture was heated under reflux for 18 hours. After cooling, the reaction mixture was filtered and the solvent was evaporated. The residue was partitioned between ethyl acetate and water. The organic fractions were combined, washed with water and brine, dried and evaporated to give the title compound as an oil. |
Here is a chemical reaction formula: Reactants are m2_m4:COC(C1=C(C=CC(=C1)OCC1=CC=CC=C1)O)=O, amount is: 0.0 ;m1:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:O1CCCC1, amount is: 0.0 ;m2_m4:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=CC(=C(C=C1)O)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Lithium aluminium hydride (0.235 g, 6.2 mMol) was suspended in tetrahydrofuran (25 ml) and cooled to 0° C. 5-Benzyloxy-2-hydroxy benzoic acid methyl ester (2 g, 7.75 mMol) in tetrahydrofuran (10 ml) was added dropwise, via cannula. The mixture was warmed to room temperature and stirred for 20 minutes. The reaction was then cooled to 0° C. and cautiously quenched by the addition of water (0.5 ml), 2M sodium hydroxide solution (0.5 ml), and water (1 ml). The resulting mixture was stirred at room temperature for 30 minutes and filtered. The filtrate was evaporated in vacuo to yield 4-benzyloxy-2-hydroxymethyl phenol as a clear oil which was used in the next step without further purification. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C1=CC=CC=C1)OC=1C=C(OC[C@@H]2CO2)C=CC1OCC1=CC=CC=C1, amount is: 0.0 MOLE;m0_m1_m2:COC(COC1=CC=C(C=C1)C[C@@H](C)N)=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(C1=CC=CC=C1)OC=1C=C(OCC(CNC(CC2=CC=C(OCC(=O)OC)C=C2)C)O)C=CC1OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from (S)-3-(3,4-dibenzyloxyphenoxy)-1,2-epoxypropane and (R)-4-(2-aminopropyl)phenoxyacetic acid methyl ester according to the method described in Procedure 13. |
Here is a chemical reaction formula: Reactants are m1_m2:COC=1C=C(C=CC1OC)C[C@@H](C)N, amount is: 0.0 ;m1_m2:Br, 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:Br.OC=1C=C(C=CC1O)C[C@@H](C)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (R)-3-(3,4-dimethoxyphenyl)-2-propylamine hydrochloride1 (500 mg, 2.15 mMol) in hydrogen bromide (48%, 5 ml) was stirred at 100° C. under an argon atmosphere for 20 hours. After cooling, the solvent was evaporated and the residue was dried giving the title compound. |
Here is a chemical reaction formula: Reactants are m1_m4_m3_m2:C(C)OC(=O)C1(OC2=C(O1)C=CC(=C2)C[C@@H](C)NC(=O)OC(C)(C)C)C(=O)OCC, amount is: 0.0 ;m1_m4_m3_m2:C(C)OCC, amount is: 0.0 ;m1_m4_m3_m2:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4_m3_m2:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.N[C@@H](CC1=CC2=C(OC(O2)(C(=O)OCC)C(=O)OCC)C=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (R)-5-[N-(t-butyloxycarbonyl)-2-aminopropyl]-1,3-benzodioxole-2,2-dicarboxylic acid diethyl ester (3.0 g, 7 mMol) in ethyl acetate (40 ml) and hydrogen chloride solution in diethyl ether (1M, 56 ml, 56 mMol) was stirred at ambient temperature under an argon atmosphere for 48 hours. The solvent was evaporated and the residue was dried giving the title compound as a glass. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:Cl.C(C)OC(=O)C1(OC2=C(O1)C=CC(=C2)C[C@@H](C)N)C(=O)OCC, amount is: 0.0 ;m1_m3_m2:C(O)([O-])=O.[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N[C@@H](CC1=CC2=C(OC(O2)(C(=O)OCC)C(=O)OCC)C=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (R)-5-(2-aminopropyl)-1,3-benzodioxole-2,2-dicarboxylic acid diethyl ester hydrochloride (646 mg, 2 mMol) in dichloromethane (80 ml) was shaken with a saturated solution of sodium hydrogen carbonate (20 ml) for 30 seconds. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×50 ml). The combined organic extracts were washed with water (50 ml) and brine (50 ml), dried (MgSO4). The solvent was evaporated giving the title compound which was used immediately. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(C)(C)OC(=O)NCCC1=CC=C(OCP(OCC)(OCC)=O)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(Cl)Cl, amount is: 0.0 ;m1_m2_m3:FC(C(=O)O)(F)F, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NCCC1=CC=C(OCP(OCC)(OCC)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(2-t-Butoxycarbonylaminoethyl)phenoxymethylphosphonic acid, diethyl ester (2.856 g, 9.95 mMol) in methylene chloride (300 ml) and trifluoracetic acid (16 ml) was stirred at room temperature for 5 h. The solution was concentrated under reduced pressure and product dried under in vacuo. The trifluoacetic acid salt was neutralized with aqueous sodium carbonate and extracted with dichloromethane containing a small proportion of methanol (5×100 ml). The combined organic layers were dried over sodium sulfate and evaporated to dryness to give the title compound as a pale yellow gum. |
Here is a chemical reaction formula: Reactants are m3:BrCC(=O)OC, amount is: 0.0 ;m1_m2_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m4:OC1=CC=C(C=C1)C[C@@H](C)NC(OC(C)(C)C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=C(OCC(=O)OC)C=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Potassium carbonate (1.95 g, 14.2 mMol) was added to a solution of (R)-2-(4-hydroxyphenyl)-1-methylethylcarbamic acid, t-butyl ester (2.96 g, 11.8 mMol) in acetone (50 ml) at room temperature under argon. Methyl bromoacetate (1.81 g, 11.8 mMol) was added dropwise and the reaction mixture was heated at reflux for 3 hours. The solvent was removed under reduced pressure and the residue was taken into ethyl acetate and washed with water (2×30 ml). The organic extracts were dried with sodium sulfate and the solvent evaporated in vacuo. The crude product was purified by chromatography on Kieselgel 60 (eluting with 20% ethyl acetate in pentane) to give the title compound as an oil. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C=C)OCC1=CC=CC=C1, amount is: 0.0 MOLE;m0_m1_m2:[PH2](O)=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(C1=CC=CC=C1)OCCCP(O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from allylbenzyl ether and 50% aqueous phosphinic acid by an analogous procedure to that described in J. Inorg. Nucl. Chem., 1965, 27, 697. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(CCC)OP(=O)CCCOCC1=CC=CC=C1, amount is: 0.0 MOLE;m0_m1_m2: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:C(C1=CC=CC=C1)OCCCP(OCCCC)(=O)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 3-benzyloxypropylphosphinic acid n-butyl ester and paraformaldehyde according to the method described in Procedure 31. Purification by chromatography, eluting with dichloromethane containing 5% methanol, gave an oil. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C1=CC=CC=C1)OCCCP(OCCCC)(=O)COS(=O)(=O)C1=CC=C(C=C1)Cl, amount is: 0.0 MOLE;m0_m1_m2:OC1=CC=C(C=C1)CCNC(OC(C)(C)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:C(C)(C)(C)OC(=O)NCCC1=CC=C(OCP(OCCCC)(=O)CCCOCC2=CC=CC=C2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 3-benzyloxypropyl-(4-chlorobenzenesulfonyloxymethyl)phosphinic acid, n-butyl ester and 2-(4-hydroxyphenyl)ethylcarbamic acid, t-butyl ester according to the procedure described in Procedure 24. The crude product was purified by chromatography, eluting with dichloromethane containing 3% methanol, to give an oil. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C1=CC=CC=C1)OCCCP(OCCCC)(=O)COS(=O)(=O)C1=CC=C(C=C1)Cl, amount is: 0.0 MOLE;m0_m1_m2:OC1=CC=C(C=C1)C[C@@H](C)NC(OC(C)(C)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:C(C)(C)(C)OC(=O)NC(CC1=CC=C(OC[P@@](OCCCC)(=O)CCCOCC2=CC=CC=C2)C=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 3-benzyloxypropyl-(4-chlorobenzenesulfonyloxymethyl)phosphinic acid, n-butyl ester and (R)-2-(4-hydroxyphenyl)-1-methylethylcarbamic acid, t-butyl ester according to the method described in Procedure 24. The crude product was purified by chromatography, eluting with dichloromethane containing 3% methanol, to give an oil. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C1(CCCCC1)P(O)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m0_m1_m2:C(CCC)O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C1(CCCCC1)P(OCCCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from cyclohexylphosphinic acid and n-butanol according the the method described in Procedure 43. The compound was used without further purification. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C1(CCCCC1)P(OCCCC)=O, amount is: 0.0 MOLE;m0_m1_m2: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:C1(CCCCC1)P(OCCCC)(=O)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from cyclohexylphosphinic acid, n-butyl ester and paraformaldehyde according to the method described in Procedure 31. Purification by chromatography, eluting with dichloromethane containing 5% methanol, gave an oil. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:NCCC1CCC(CC1)P(OCCCC)(=O)COC1=CC=CC=C1, amount is: 0.0 MOLE;m0_m1_m2:C(C1=CC=CC=C1)OC1=CC=C(OC[C@H]2OC2)C=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:C(C1=CC=CC=C1)OC1=CC=C(OCC(CNCCC2CCC(CC2)[P@@](OCCCC)(=O)COC2=CC=CC=C2)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 4-(2-aminoethyl)phenoxy methylcyclohexylphosphinic acid, n-butyl ester and (S)-2-(4-benzyloxyphenoxymethyl)oxirane according to the method described in Procedure 13. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C=CCCCC, amount is: 0.0 MOLE;m0_m1_m2:[PH2](O)=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(CCCCC)P(O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from n-hexene and 50% aqueous phosphinic acid by an analogous procedure to that described in J. Inorg. Nucl. Chem., 1965, 27, 697. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(CCCCC)P(O)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m0_m1_m2:C(CCC)O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(CCCCC)P(OCCCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from n-hexylphosphinic acid and n-butanol according the the method described in Procedure 43. The compound was used without further purification. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(CCCCC)P(OCCCC)=O, amount is: 0.0 MOLE;m0_m1_m2: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:C(CCCCC)P(OCCCC)(=O)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from n-hexylphosphinic acid, n-butyl ester and paraformaldehyde according to the method described in Procedure 31. Purification by chromatography, eluting with dichloromethane containing 5% methanol, gave an oil. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:NCCC1=CC=C(C=C1)O, amount is: 0.0 MOLE;m0_m1_m2:C(C1=CC=CC=C1)OC1=CC=C(OC[C@H]2OC2)C=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:C(C1=CC=CC=C1)OC1=CC=C(OC[C@H](CNCCC2=CC=C(C=C2)O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from tyramine and (S)-2-(4-benzyloxyphenoxymethyl)oxirane according to the method described in Procedure 13. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:C(C1=CC=CC=C1)OC1=CC=C(OC[C@H](CNCCC2=CC=C(C=C2)O)O)C=C1, amount is: 0.0 ;m1_m2_m4_m3:C(C1=CC=CC=C1)Br, amount is: 0.0 ;m1_m2_m4_m3:C([O-])([O-])=O.[Na+].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N(CCC1=CC=C(C=C1)O)C[C@@H](COC1=CC=C(C=C1)OCC1=CC=CC=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (S)-1-(4-benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol (1.9 g, 4.8 mMol) and benzyl bromide (0.57 ml, 4.8 mMol) in dimethylformamide (10 ml) containing sodium carbonate (770 mg, 7.2 mMol) was stirred at room temperature for 18 hours. The mixture was filtered and the residue was washed with ethyl acetate. The filtrates were combined, washed with water and brine, dried and evaporated. Purification of the residue by flash chromatography (silica gel, 50% ethyl acetate in hexane) gave the title compound. |
Here is a chemical reaction formula: Reactants are m3:C(C1=CC=CC=C1)Cl, amount is: 0.0 ;m1_m2:[PH2]([O-])=O.[NH4+], amount is: 0.0 ;m1_m2:C[Si](N[Si](C)(C)C)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)P(OCCCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of ammonium phosphinate (9.18 g) and hexamethyldisilazane (25 mL) was heated at 110° C. for 2 hours. The mixture was cooled in ice, dissolved in dry dichloromethane (120 mL), benzyl chloride (20 g; 14 mL) was added and the mixture allowed to warm to room temperature and stirred 18 hours. The solution was filtered, the solvent evaporated, the residue azeotroped with methanol (2×70 mL), dissolved in toluene (150 mL) containing n-butanol (30 mL) and the solution was boiled under reflux in a Dean and Stark water trap for 5 hours. The solvent was evaporated, the residue slurried with dichloromethane (120 mL), filtered and evaporated and the residue chromatographed on silica-gel in 1-2% methanol in dichloromethane to give the title compound as an oil. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C1=CC=CC=C1)P(OCCCC)=O, amount is: 0.0 MOLE;m0_m1_m2: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:C(C1=CC=CC=C1)P(OCCCC)(=O)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from benzylphosphinic acid, n-butyl ester and paraformaldehyde according to the method described in Procedure 31. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C1=CC=CC=C1)P(OCCCC)(=O)CO, amount is: 0.0 MOLE;m0_m1_m2:ClC1=CC=C(C=C1)S(=O)(=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(C1=CC=CC=C1)P(OCCCC)(=O)COS(=O)(=O)C1=CC=C(C=C1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from benzylhydroxymethylphosphinic acid, n-butyl ester and 4-chlorobenzenesulfonyl chloride according to the method described in Procedure 32. The resulting white solid (mp 87°-88° C.) was used in the next stage without further purification. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:Cl.OC(CNC(CC1=CC=C(OCC(=O)OC)C=C1)C)COC1=CC(=C(C=C1)O)O, amount is: 0.0 ;m1_m3_m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.OC=1C=C(OCC(CNC(CC2=CC=C(OCC(=O)O)C=C2)C)O)C=CC1O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (SR)-4-{2-[2-hydroxy-3-(3,4-dihydroxyphenoxy)propylamino]propyl}phenoxyacetic acid, methyl ester, hydrochloride (78 mg, 0.17 mMol) in water (2 ml) containing hydrochloric acid (1M, 0.5 ml, 0.51 mMol) was heated at 100° C. under argon for 3 hours. After cooling to room temperature the solution was freeze dried giving the title compound as a colourless solid. |
Here is a chemical reaction formula: Reactants are m1:OC(CNCCC1=CC=C(OC[P@](OCCCC)(=O)CCCOCC2=CC=CC=C2)C=C1)COC1=CC(=C(C=C1)O)CO, amount is: 0.0 MOLE;m2: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:O[C@@H](CNCCC1=CC=C(OCP(O)(=O)CCCOCC2=CC=CC=C2)C=C1)COC1=CC(=C(C=C1)O)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from (S)-4-{2-[2-hydroxy-3-(4-hydroxy-3-hydroxymethyl-phenoxy)propylamino]ethyl}phenoxymethyl-(3-benzyloxypropyl)phosphinic acid, n-butyl ester according to a modification of the procedure described in Example 5. Acidification to pH 3.5 with 1M hydrochloric acid followed by C18 reverse phase chromatography, eluting with water-methanol (30%) and freeze drying of the resultant foam gave the title compound as a solid. |
Here is a chemical reaction formula: Reactants are m2:Cl, amount is: 0.0 MOLE;m1:OC(CNC(CC1=CC=C(OCP(OCCCC)(=O)CCCOCC2=CC=CC=C2)C=C1)C)COC1=CC(=C(C=C1)O)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:Cl.OC(CNC(CC1=CC=C(OCP(O)(=O)CCCOCC2=CC=CC=C2)C=C1)C)COC1=CC(=C(C=C1)O)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from (SR)-4-{2-[2-hydroxy-3-(4-hydroxy-3-hydroxymethylphenoxy)propylamino]propyl}phenoxymethyl(3-benzyloxypropyl)phosphinic acid, n-butyl ester according to a modification of the procedure described in Example 5. Acidification to pH 3.5 with 1M hydrochloric acid followed by C18 reverse phase chromatography, eluting with water-methanol (30%) and freeze drying of the resultant foam gave the title compound as a solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:OC(CNCCC1CCC(CC1)[P@@](OCCCC)(=O)COC1=CC=CC=C1)COC1=CC=C(C=C1)OCC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:CO, amount is: 0.0 ,Catalysts are m1_m2_m3:[Pd], amount is: 0.0 .Products are 0:OC(CNCCC1CCC(CC1)[P@@](OCCCC)(=O)COC1=CC=CC=C1)COC1=CC=C(C=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (S)-4-{2-[2-hydroxy-3-(4-benzyloxyphenoxy)propylamino]ethyl}phenoxymethylcyclohexylphosphinic acid, n-butyl ester (1.00 g, 1.64 mMol) in methanol (100 ml) containing 10% palladium on charcoal (50 mg) was hydrogenated at 40° C. and 40 p.s.i. for 24 hours. After cooling to room temperature the suspension was filtered through a pad of filter aid and the filtrate was evaporated giving the title compound. |
Here is a chemical reaction formula: Reactants are m1:OC(CNCCC(CCC[P@@](OCCCC)(=O)COC1=CC=CC=C1)CC)COC1=CC=C(C=C1)O, amount is: 0.0 MOLE;m2: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:OC(CNCC[C@H](CCCP(O)(=O)COC1=CC=CC=C1)CC)COC1=CC=C(C=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from (S)-4-{2-[2-hydroxy-3-(4-hydroxyphenoxy)propylamino]ethyl}phenoxymethyl-n-hexyl phosphinic acid, n-butyl ester according a modification of the procedure described in Example 25. Acidification to pH 6 with 1M hydrochloric acid followed by C18 reverse phase chromatography and freeze drying gave the title compound as a solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m5_m3:C(C1=CC=CC=C1)(=O)OCOCN1C(=O)NC(=O)C(C)=C1, amount is: 0.0 ;m1_m2_m5_m3:C(C)C(OP(=O)(O)O)CC, amount is: 0.0 ;m1_m2_m5_m3:FC(S(=O)(=O)O[Si](C)(C)C)(F)F, amount is: 0.0 ;m4:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5_m3:C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)OP(=O)(OCC)COCOCN1C(=O)NC(=O)C(C)=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1-[(benzoyloxy)methoxymethyl]thymine (2.9 g, 10 mmol) and diethyl phosphonomethanol (1.85 g, 11 mmol) in benzene (180 mL) was added trimethylsilyl trifluoromethanesulfonate (0.05 mL) via a syringe under nitrogen. The solution was heated at 85° C. for 20 min. After cooling to room temperature, ethyl acetate (50 mL) was added and washed with aqueous bicarbonate, brine dried (MgSO4), filtered and concentrated in vacuo. The resultant yellow oil was purified by silica gel column chromatography using CH2Cl2 /5% MeOH as an eluent to give the title compound as a white oil: yield 980 mg (30%). |
Here is a chemical reaction formula: Reactants are m1:C1(=CC=CC=C1)[Se]CCO, amount is: 0.0 ;m3:C(Cl)Cl, amount is: 0.0 ;m2: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:C1(=CC=CC=C1)[Se]CCOCCl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-(phenylselenyl)ethanol (4.0 g, 20 mmol) [prepared according to the literature procedure: P. Rollin, V. V. Bencomo, P. Sinay, Synthesis, 13 (1984)] in CH2Cl2 (15 mL) was added paraformaldehyde (620 mg, 20 mmol). HCl gas was then bubbled into the solution at 5° C. for 2 hr. The solution was dried (MgSO4), and the solvent was removed under reduced pressure to give the title compound as a colorless oil in a quantitative yield. |
Here is a chemical reaction formula: Reactants are m1_m5_m2_m3:C(C)(=O)NC1=NC(=C2N=CN(C2=N1)COCC[Se]C1=CC=CC=C1)C(N(C1=CC=CC=C1)C1=CC=CC=C1)=O, amount is: 0.0 ;m1_m5_m2_m3:OO, amount is: 0.0 ;m1_m5_m2_m3:C([O-])(O)=O.[Na+], amount is: 0.0 ;m4:C(C)(C)N(CC)C(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m3:O1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)NC1=NC(=C2N=CN(C2=N1)COC=C)C(N(C1=CC=CC=C1)C1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-acetamido-6-diphenylcarbamoyl-9-[2-(phenylselenyl)ethoxymethyl]purine (4.92 g, 8.16 mmol) in dioxane (80 mL) was added 30% H2O2 (4 mL, 35 mmol) and sodium bicarbonate (2.1 g, 24.5 mmol). The mixture was heated at 60° C. for 20 min. The reaction was then concentrated to about 10 mL, diluted with ethyl acetate (100 mL), dried (MgSO4) and the solvents were removed in vacuo. The residue was dissolved in dioxane (40 mL), diisopropylethylamine (1.27 g, 10 mmol) was added and the solution was heated at 80° C. for 30 min under nitrogen. The solvent was evaporated in vacuo and the residual oil was chromatographed on silica gel using CH2Cl2 -ethyl acetate (1:1) as eluent to give the title compound as a yellowish powder: yield 2.3 g (65%). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=CC=C(C(=O)CCC(=O)O)C=C1, amount is: 0.0 ;m1_m3_m2:O.NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1CCC(NN1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-(4-chlorobenzoyl)propionic acid (20 g) in absolute ethanol (200 ml) was added 5 g of hydrazine monohydrate. A thick solid was formed which dissolved after heating. The resulting solution was refluxed for 3 h, cooled and the solid formed filtered and dried to yield 16 g (80%) of 6-(4-chlorophenyl)-4,5-dihydropyridazinone. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:ClC1=CC=C(C(=O)C(C(=O)O)C)C=C1, amount is: 0.0 ;m1_m4_m2_m3:C(C)(=O)[O-].[Na+], amount is: 0.0 ;m1_m4_m2_m3:Cl.C(C)(C)(C)NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:C(CCC)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1CCC(N(N1)C(C)(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-chlorobenzoylpropionic acid (4.24 g) in n-butanol (150 ml) was added anhydrous sodium acetate (1.54 g) and t-butylhydrazine hydrochloride (2.75 g) portionwise at room temperature. The resulting mixture was refluxed for 9 hours distilling off 65 ml of n-butanol during that time. The resulting mixture was cooled and poured into water (500 ml) and extracted with methylene chloride (3×150 ml). The combined organic layers were washed with 2% aqueous sodium hydroxide (3×100 ml), water (2×100 ml), 2% aqueous hydrochloric acid (3×100 ml), and water (1×100 ml), dried and evaporated under vacuum yielding 1.71 g of the expected product. |
Here is a chemical reaction formula: Reactants are m1_m4:CC1=CC=C(C(=O)CCC(=O)O)C=C1, amount is: 0.0 ;m2:[Cl-].[Al+3].[Cl-].[Cl-], amount is: 0.0 ;m3:ClCl, 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:ClC=1C=C(C(=O)CCC(=O)O)C=C(C1C)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 3-(4-methylbenzoyl)propionic acid (7.5 g) and methylene chloride (250 ml) was added slowly portionwise aluminum chloride (15 g) at 0° C. After the addition was completed chlorine gas was bubbled in slowly at 0° C. After 6 hours the reaction mixture was poured into a mixture of hydrochloric acid and ice and extracted with methylene chloride (3×150 ml), the combined organic layers were washed with water, dried and evaporated under vacuum yielding 3-(3,5-dichloro-4-methylbenzoyl)propionic acid as a yellow solid (4.5 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m5:C(C#CCO)O, amount is: 0.0 ;m2:O1CCCC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CCOCC, amount is: 0.0 MOLE;m1_m3_m5:CCOCC, amount is: 0.0 ,Catalysts are m1_m3_m5:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 .Products are 0:O1C(CCCC1)OCC#CCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic acid and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC1=CC=C(C=C1)C=1CCC(NN1)=O, amount is: 0.0 ;m1_m2_m3:C(C)(=O)O, amount is: 0.0 ;m1_m2_m3:BrBr, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1C=CC(NN1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 6-(4-chlorophenyl)-4,5-dihydropyridazinone (11.75 g) and glacial acetic acid (100 ml) was added dropwise 3 ml of bromine and the mixture was heated at 60°-70° C. for 3 h. The resulting mixture was cooled and slowly poured into 400 ml of cold water. The resulting white solid was filtered and dried to yield 10.83 g (89%) of 6-(4-chlorophenyl)pyridazinone. |
Here is a chemical reaction formula: Reactants are m2_m3:O, amount is: 0.0 ;m2_m3:Cl, amount is: 0.0 ;m1_m4_m5:ClC1(C(C(C1)(F)F)(F)Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m5:CCOCC, amount is: 0.0 ;m1_m4_m5:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1(C(C=C1Cl)(F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1,1,2 trichloro-2,3,3-trifluorocyclobutane (55.5 g) in 100 ml of anhydrous ether, triethylamine (40 ml) was added dropwise over 30 min at room temperature, and the mixture was stirred overnight at ambient temperature. The mixture was then stirred with 120 ml H2O and 7.5 ml of concentrated HCl. The ether layer was washed with H2O (100 ml), brine (100 ml), dried over anhydrous MgSO4, and evaporated in vacuo. The residue was distilled fractionally at atmospheric pressure from 64°-68° C. to yield 36 g (79%) of a colorless liquid as pure product. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC(C(C(=O)O)(F)F)(C(=O)O)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:O1CCOCC1, amount is: 0.0 ,Catalysts are m1_m2_m3:[Zn], amount is: 0.0 .Products are 0:FC(C(=O)O)(C(C(=O)O)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirring solution of the chlorotrifluorosuccinic acid (part b) (24.5 g) in 200 ml dioxane was added portionwise zinc metal (85 g) and the mixture was stirred at ambient temperature for 10 hours to yield a viscous liquid which was decanted from the unreacted zinc. Most of the dioxane was evaporated in vacuo. The residue was dissolved in 100 ml H2O and a solution of 7.7 ml of concentrated H2SO4 in 25 ml of water was added. The solution was extracted with ether (3×100 ml) and dried over anhydrous MgSO4. The organic layer was stripped to yield 8.3 g (32%) of the product as a crystalline solid. |
Here is a chemical reaction formula: Reactants are m2:O, amount is: 0.0 MOLE;m1_m4_m3:C(C1=CC=CC=C1)(=O)CCCC(=O)O, amount is: 0.0 ;m1_m4_m3:NN, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6:C1(=CC=CC=C1)C, amount is: 0.0 MOLE;m1_m4_m3:C1(=CC=CC=C1)C, amount is: 0.0 ;m5:CCOCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)C1=CC=CC(N=N1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 10 g (0.052 mole) of 4-benzoylbutyric acid in 300 ml of toluene, hydrazine was added in one portion and the reaction was heated to reflux until all water had ceased to azeotrope. The reaction mixture was cooled and the toluene was stripped off in vacuo. The residue was dissolved in 200 ml Et2O and washed with H2O (100 ml) and brine (100 ml). The ether extract was dried over anhydrous MgSO4, filtered and stripped to yield an orange semisolid which was triturated with ether to yield 3.8 g (39%) of the desired product as a yellow solid. |
Here is a chemical reaction formula: Reactants are m3:[H][H], amount is: 0.0 MOLE;m4:COC(OC)=O, amount is: 0.0 ;m1_m6_m2_m5:[H-].[Na+], amount is: 0.0 ;m1_m6_m2_m5:ClC=1C=C2CCC(C2=CC1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6_m2_m5:C(OC)COC, amount is: 0.0 ;m1_m6_m2_m5:C(OC)COC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of sodium hydride (2.4 g, 60% in mineral oil, 0.06 mole) and 50 ml dry dimethoxyethane, 5-chloroindanone (50 g, 0.03 mole) in 50 ml dimethoxyethane was added dropwise at room temperature. The mixture was stirred at room temperature until hydrogen evolution ceased. Then dimethylcarbonate (27 g, 0.3 mole) was added dropwise at room temperature and the reaction was heated to 60° C. for one hour. The reaction was cooled to room temperature, quenched with 100 ml H2O, acidified to pH 5 with concentrated HCl and extracted with ethyl ether (3×100 ml). The ether extract was washed with brine (100 ml), dried over anhydrous MgSO4 and stripped to yield 3.0 g (45%) of the desired product as a tan solid. |
Here is a chemical reaction formula: Reactants are m1:P(=O)(Cl)(Cl)Cl, amount is: 0.0 ;m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 MOLE;m2:CN(C)C=O, amount is: 0.0 ;m3:ClC1=CC=C(C=C1)CC(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C(C=O)=CN(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phosphorus oxychloride (92 g) was added dropwise to stirred DMF (78 ml) between 10°-15° C. To the resulting slurry was added 4-chlorophenylacetic acid (34.12 g). The resulting mixture was stirred at room temperature for one half hour and then heated to 70°-80° C. during 5.5 hours, during which time the mixture became effervescent. The reaction mixture was cooled and poured slowly onto cracked ice. The resulting suspension was brought to pH 10 with solid potassium carbonate. Ice was added intermittently during this addition to maintain the temperature below 15° C. Toluene (150 ml) was added and the resulting mixture heated at 100° C. for one hour. The mixture was cooled and allowed to stand overnight. The two resulting layers were separated and the aqueous layer extracted with toluene (2×100 ml). The combined organic layers were washed with water (5×200 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo and the resulting yellow solid was triturated with hexane to yield 26 g of 2-(4-chlorophenyl)-3-dimethylaminopropenal as a tan solid top. 120°-125° C. |
Here is a chemical reaction formula: Reactants are m4:C(C)(=O)O, amount is: 0.0 ;m3:ClC1=CC=C(C=C1)C(C=O)=CN(C)C, amount is: 0.0 MOLE;m1_m5_m2:C[O-].[Na+], amount is: 0.0 ;m1_m5_m2:C(#N)CC(=O)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 ;m1_m5_m2:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To solution of sodium methoxide (7.52 g) in methanol (130 ml) was added cyanoacetamide (5.84 g) followed by 2-(4-chlorophenyl)-3-dimethylaminopropenal and the resulting suspension was refluxed overnight. During this time a yellow solid was formed. The mixture was cooled to room temperature and glacial acetic acid (50 ml) was added followed by water (100 ml). The resulting yellow orange solid was filtered off, washed several times with water and dried to yield 8.1 g of 3-cyano-5-(4-chlorophenyl)-2-pyridinone. |
Here is a chemical reaction formula: Reactants are m3_m5:C(C=CC1=CC=CC=C1)(=O)Cl, amount is: 0.0 ;m4:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m6_m2:ClC1=CC=C(N)C=C1, amount is: 0.0 ;m1_m6_m2:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:O, amount is: 0.0 ;m3_m5:C1(=CC=CC=C1)C, amount is: 0.0 ;m1_m6_m2:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)NC(C=CC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 4-chloroaniline (16.2 g), toluene (120 ml), and pyridine (11 ml) at 0° C., cinnamoyl chloride (20.0 g) in 120 ml of toluene was added dropwise. After stirring 15 minutes at 0° C. the reaction mixture was poured into a mixture of ethyl acetate: water (250 ml:250 ml). The organic layer was separated and extracted with 5% aqueous HCl (3×250 ml), water (1×250 ml), 5% aqueous sodium bicarbonate (3×250 ml), dried over anhydrous sodium sulfate and evaporated yielding the amide as a white solid. |
Here is a chemical reaction formula: Reactants are m2:N1C(C=CC2=CC=CC=C12)=O, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ;m4:[Cl-].[NH4+], amount is: 0.0 ;m3:BrCC#CCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6_m0:CCCCCC, amount is: 0.0 MOLE;m1_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C2C=CC(N(C2=CC=C1)CC#CCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of NaH (60% in mineral oil, 700 mg) in dry DMF (100 ml) at 0° C. was added the preceding quinolinone (2.05 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (1.6 g) dropwise. The resulting mixture was kept at 0° C. for one half hour and poured into saturated aqueous ammonium chloride (200 ml). The aqueous suspension was extracted with ether (3×100 ml), the combined ether layers washed with brine and dried, yielding the crude product. Trituration with hexane yielded the product as a yellow solid (1 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m6_m5:ClC1=CC=C(C=C1)C(C=O)=CN(C)C, amount is: 0.0 ;m1_m2_m3_m6_m5:NC(=O)N, amount is: 0.0 ;m1_m2_m3_m6_m5:Cl, amount is: 0.0 ;m4:[Cl-].[NH4+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m6_m5:C(C)O, amount is: 0.0 ;m1_m2_m3_m6_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1C=NC(NC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-(4-chlorophenyl)dimethylaminopropenal (Example 145a) (5.13 g), urea (2.4 g), concentrated HCl (10 ml), water (4 ml) and ethanol (150 ml) was refluxed for 4 hours. After cooling to room temperature concentrated ammonium chloride was added until the pH was 7. The resulting yellow solid was filtered off and dried yielding 1.5 g of 5-(4-chlorophenyl)-2-pyrimidinone. |
Here is a chemical reaction formula: Reactants are m5_m0:CCCCCC, amount is: 0.0 MOLE;m4:[Cl-].[NH4+], amount is: 0.0 ;m1_m6:[H-].[Na+], amount is: 0.0 ;m3:BrCC#CCC, amount is: 0.0 ;m2:N1C(C=CC=C1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1C=NC(N(C1)CC#CCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of NaH (60% in mineral oil, 340 mg) in dry DMF (75 ml) at 0° C. was added the preceding pyridinone (1.0 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (750 mg) dropwise. The resulting mixture was kept at 0° C. for one half hour and poured into saturated aqueous ammonium chloride (200 ml). The aqueous suspension was extracted with ether (3×100 ml), the combined ether layers washed with brine and dried, yielding the crude product. Trituration with hexane yielded the product as a yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=CC=C(C=C1)C=1C=CC(NN1)=O, amount is: 0.0 ;m1_m3_m2:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1C=CC(NN1)=S, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3.0 g of 6-(4-chlorophenyl)-pyridazinone, 50 ml of dry pyridine and 3.2 g of phosphorus pentasulfide was refluxed for 1 hour, evaporated to dryness and extracted with 200 ml of ether. The ether extract was washed with water (3×100 ml), brine (100 ml), dried over magnesium sulfate and evaporated to yield 3.0 g of 6-(4-chlorophenyl)-pyridazinthione as a yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=CC=C(C(=O)NN)C=C1, amount is: 0.0 ;m1_m3_m2:ClCC(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:O1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCC(=O)NNC(C1=CC=C(C=C1)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of p-chlorobenzoic hydrazide (11.2 g) in dioxane (100 ml) was added chloroacetyl chloride (6 ml). The resulting mixture was refluxed for three hours, cooled to room temperature and filtered. The resulting solid was washed with ethyl ether and dried to yield N'-chloroacetyl-4-chlorobenzoic hydrazide as white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:BrCC(=O)C1=CC=C(C=C1)Cl, amount is: 0.0 ;m1_m2_m3:COC(=S)NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C1=NNC(SC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-bromo-p-chloroacetophenone (9.16 g), methoxythiocarbonylhydrazine (13.0 g) and acetonitrile (75 ml) was refluxed overnight and then cooled and filtered. The light yellow solid was washed with hexane and dried yielding 5-(4-chlorophenyl)-3H,6H-1,3,4-thiadiazin-2-one (4.3 g). |
Here is a chemical reaction formula: Reactants are m2:CNN, amount is: 0.0 ;m1:ClC1=CC=C(C(=O)CCC(=O)O)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1CCC(N(N1)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a 250 ml flask equipped with magnetic stirrer and reflux condenser was charged 10 g of 3-(4-chlorobenzoyl)-propionic acid, 250 ml. of absolute ethanol, and 2.5 ml of methyl hydrazine. The reaction was refluxed for 3 hours and cooled to yield a solid which was collected by vacuum filtration, washed with 50 ml of hexane, and air dried. Isolated 9.5 g of product as a white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=CC=C(C=O)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(CCC(=O)C)(=O)O, amount is: 0.0 ;m1_m2_m3_m4:N1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=CC(=O)CCC(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a dry 250 ml flask equipped with a magnetic stirrer, Dean-Stark trap, and reflux condenser was charged 15 g of 4-chlorobenzaldehyde, 12.4 g levulenic acid, 5.7 ml of piperidine, and 100 ml of toluene. The reaction was refluxed for 3 hours, after which no water was observed to azeotrope from the solution. The reaction was cooled and stripped to yield a reddish-brown liquid which was triturated with hexane to yield 11.2 g of product as a yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:[N+](=O)([O-])C=1C(=C(C(=O)[O-])C=CC1OC)C, amount is: 0.0 ;m1_m3_m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a 500 ml erlenmeyer flask with magnetic stirrer was charged 10.3 g of 3-nitro-4-methoxy-methylbenzoate, 400 ml tetrahydrofuran, and 3.2 g of 86% potassium hydroxide. The reaction was stirred for 12 hours at ambient temperature, after which the resulting solid was collected by vacuum filtration and washed with 2×100 ml of ethyl ether. The solid was dissolved in 200 ml of water and acidified to pH 4 with 6N hydrochloric acid. The resulting precipitate was collected by vacuum filtration, washed with 200 ml water, and dried overnight in vacuo at 30° C. Isolated 7.4 g of product as a white solid. |
Here is a chemical reaction formula: Reactants are m3:FC(C(=O)O)(F)F, amount is: 0.0 ;m1_m4_m2:N([C@H](CC1=CC=CC=C1)C(=O)N1[C@H](C(=O)OCC2=CC=CC=C2)CCC1)C(=O)OC(C)(C)C, amount is: 0.0 ;m1_m4_m2:C1(=CC=CC=C1)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N[C@H](CC1=CC=CC=C1)C(=O)N1[C@H](C(=O)OCC2=CC=CC=C2)CCC1.FC(F)(F)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirring solution of Boc-D-Phe-Pro-OBn (68 g, 150 mmol) in dichloromethane (50 mL) at 0° C., was added anisole (20 mL) followed by trifluoroacetic acid (400 mL). After stirring for 3 hours, the solvents were evaporated in vacuo and the thick oily residue was dissolved in diethyl ether (1.5 L) and refrigerated (72 hours). The white precipitate was filtered, washed with diethyl ether (300 mL) and dried to yield 59.4 g (85%) of white powder. |
Here is a chemical reaction formula: Reactants are m1_m3_m4_m5_m2:C1(=NC=CC2=CC=CC=C12)C(=O)O, amount is: 0.0 ;m1_m3_m4_m5_m2:[H][H], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3_m4_m5_m2:CCO, amount is: 0.0 ;m1_m3_m4_m5_m2:Cl, amount is: 0.0 ,Catalysts are m1_m3_m4_m5_m2:[Rh], amount is: 0.0 .Products are 0:C1(NCCC2CCCCC12)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1-isoquinolinecarboxylic acid (50 g, 0.288 mol) in EtOH (150 mL) and 60 mL of 5N HCl was reduced over 5% Rh/Al2O3 (14 g) at 52 bar (750 psi) of hydrogen in a high pressure apparatus at 50° C. for 17 hours. The reaction mixture was filtered through a pad of diatomaceous earth, and the filtrate was concentrated in vacuo. The solid was triturated with water, filtered and dried to give DL-perhydro-1-isoquinolinecarboxylic acid (DL-1-Piq-OH) (30 g, 48%) FD-MS 184 (MH+). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:Cl, amount is: 0.0 MOLE;m1_m2_m3:N1[C@@H](CC2=CC=CC=C12)C(=O)O, amount is: 0.0 ;m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)OC(=O)[C@H]1NC2=CC=CC=C2C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: HCl gas was bubbled through a stirring suspension of (S)-indoline-2-carboxylic acid (20 g, 110 mmol) in ethanol (500 mL). When the acid was completely dissolved, the solution was brought to reflux. After 16 hours, the solution was cooled and the solvent removed in vacuo. The residue was triturated with diethyl ether and the resulting off-white solid was collected by filtration, washed with hexanes and dried overnight in a vacuum oven at 30° C. to give (S)-indoline-2-carboxylic acid ethyl ester.HCl (25.7 g, 78%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(#N)C1=CC=C(/C=C/C(=O)OC)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C1(=CC=CC=C1)C, amount is: 0.0 ,Catalysts are m1_m2_m3:[Pd].[O-]S(=O)(=O)[O-].[Ba+2], amount is: 0.0 .Products are 0:C(#N)C1=CC=C(CCC(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of methyl p-cyano-trans-cinnamate (13.6 g, 73 mmol) in toluene (485 mL) was added 5% Pd/BaSO4 (2.7 g). After 9 hours under hydrogen gas at 4 bar (60 psi), the solution was filtered, concentrated in vacuo and chromatographed over silica gel, eluting with a step gradient of hexanes through 30% ethyl acetate/hexanes. The product containing fractions were combined and concentrated to give 10.6 g (77%) of colorless oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m5_m3:C(CC1=CC=CC=C1)N, amount is: 0.0 ;m1_m2_m5_m3:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m5_m3:ClC(=O)OC, amount is: 0.0 ;m7_m4:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5_m3:C1CCOC1, amount is: 0.0 ;m7_m4:C(C)OCC, amount is: 0.0 ;m6:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(=O)NCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of phenethylamine (75.2 mL, 0.6 mol) and triethylamine (83 mL, 0.6 mol) in THF (500 mL) was added slowly methyl chloroformate 46.2 mL, 0.6 mol) dissolved in THF (50 mL). After the reaction was stirred for an additional 1 h at room temperature, diethyl ether (2 L) and 1N HCl (800 mL) were added. The organic layer was washed with water, dried (MgSO4), filtered, and the filtrate was concentrated in vacuo to give a clear oil of pure title compound (102 g, 95%). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C)(C)(C)OC(=O)C1N(CCC2CCCCC12)C(=O)OC, amount is: 0.0 ;m1_m3_m2:[O-]CC.[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CCO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)OC(=O)C1N(CCC2CCCCC12)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-methoxycarbonyl-(1RS,4aSR,8aSR)-perhydoisoquinoline-1-carboxylic acid t-butyl ester (81.2 g, 273 mmol) in EtOH (500 mL) was added sodium ethoxide (21% in ethanol) (88.4 mL, 273 mmol) and the reaction mixture was refluxed (24 h). The organic solvent was evaporated in vacuo, ethyl acetate (400 mL) and water (100 mL) was added to the residue. The organic layer was separated, washed twice with water, dried (MgSO4), filtered, and the filtrate was concentrated in vacuo to afford an oil of pure title compound (70 g,0.95%); FAB-MS 270 (MH+); TLC Rf (A) 0.61. |
Here is a chemical reaction formula: Reactants are m2:C(=O)=O.CC(=O)C, amount is: 0.0 MOLE;m5:CN(C=O)C, amount is: 0.0 ;m6:C(CC(O)(C(=O)O)CC(=O)O)(=O)O, amount is: 0.0 ;m3:C(CCC)[Li], amount is: 0.0 ;m4_m7:S1C(=CC=C1)C#N, amount is: 0.0 ;m1_m8:C(C)(C)NC(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m7:C1CCOC1, amount is: 0.0 ;m9:O, amount is: 0.0 ;m1_m8:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C=1SC(=CC1)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a flame-dried 3 neck 1 L round bottom flask was added diisopropylamine (9 mL, 66 mmol) and THF (150 mL) under a nitrogen atmosphere. The flask was cooled to an internal temperature of -78° C. (dry ice/acetone). To this stirring solution was added n-butyllithium (1.6M in hexanes, 41.3 mL, 66.1 mmol) via syringe and the mixture was allowed to stir for 5 min. To this solution was added a solution of 2-thiophenecarbonitrile (6.55 g, 60 mmol) in THF (30 mL) over 10 min. The resulting bright red solution was allowed to stir at -78° C. for 45 min, at which time dimethylformamide (23.3 mL, 300 mmol) was added via syringe. This mixture was allowed to stir for 2 h at -78° C. and then solid citric acid (about 10 g) was added followed by water (60 mL). Volatile solvents were removed in vacuo and the residue was partitioned between diethyl ether and brine (200 mL each). Layers were separated and the aqueous phase was washed once with diethyl ether. The combined organic phase was washed once with brine, dried (MgSO4), filtered and concentrated in vacuo to give a yellow solid which was purified by silica gel chromatography using an ethyl acetate/hexanes gradient (hexanes to 50% ethyl acetate/hexanes). Fractions containing pure product were pooled and concentrated in vacuo to give 6.9 g (84%) of 2-cyano-5-formyl-thiophene. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(#N)C=1SC(=CC1)C=O, amount is: 0.0 ;m1_m3_m2:[BH4-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CCO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C=1SC(=CC1)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-cyano-5-formyl-thiophene (6.9 g, 50 mmol) in EtOH (100 mL) was added sodium borohydride (1.9 g, 50 mmol) in portions. After 5 min of stirring, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and brine. The layers were separated and the organic phase was washed once with 1M citric acid and once with brine, then dried (MgSO4), filtered and concentrated in vacuo to give 6.1 g (88%) of 2-cyano-5-(hydroxymethyl)thiophene. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:C(#N)C=1SC(=CC1)CO, amount is: 0.0 ;m1_m4_m2_m3:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m4_m2_m3:C(Br)(Br)(Br)Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C=1SC(=CC1)CBr, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-cyano-5-(hydroxymethyl)thiophene (6.0 g, 43 mmol) in THF (50 mL) was added triphenylphosphine (15.7 g, 47 mmol) and carbon tetrabromide (12.3 g, 47 mmol). After stirring overnight under nitrogen atmosphere at room temperature, the solvent was removed in vacuo and the residue was dissolved in chloroform, then adsorbed onto silica gel and loaded onto a silica gel column. The product was eluted using an ethyl acetate/hexanes gradient. Fractions containing pure product (as judged by TLC) were pooled and concentrated in vacuo to give 6.5 g (75%) of 2-cyano-5-(bromomethyl)thiophene. |
Here is a chemical reaction formula: Reactants are m3:BrCC1=CC=C(C#N)C=C1, amount is: 0.0 ;m1_m5_m2:[H-].[Na+], amount is: 0.0 ;m1_m5_m2:N1C(NCC1)=O, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m2:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C1N(CCN1CC1=CC=C(C#N)C=C1)CC1=CC=C(C#N)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To sodium hydride (2.4 g, 60 mmol) in dimethylformamide (50 mL) at 0° C. was added imidazolin-2-one (2.6 g, 30 mmol). After stirring for 20 minutes 4-(bromomethyl)benzonitrile (13 g, 66 mmol) was added and the mixture was warmed to ambient temperature. After stirring for 1 hour the reaction was poured into water and a solid formed. The solid was filtered to give 4,4'-[(2-oxoimidazolin-1,3-diyl)bis(methylene)]-bis(benzonitrile). NMR (CDCl3) 7.65 (d,4), 7.4 (d,4), 4.45 (s,4), 3.2 (s,4) ppm. B. In a similar manner, the following compounds were made: |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O, amount is: 0.0 ;m1_m2_m3_m4:BrCC=1C=C(C#N)C=CC1, amount is: 0.0 ;m1_m2_m3_m4:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a manner similar to Preparation 1 above, 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (1.2 g, 5 mmol) was reacted with 3-(bromomethyl)benzonitrile (0.39 g, 2 mmol) and sodium hydride (0.18 g, 5 mmol) in dimethylformamide (20 mL) to give 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile after chromatography on silica; NMR (DMSO-d6) 11.02 (s,1), 7.4 (m,4), 7.3 (m,2), 7.2 (m,7), 4.75 (s,2) ppm. |
Here is a chemical reaction formula: Reactants are m3_m7:BrCC=1C=C(C(=O)OC)C=CC1, amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE;m1_m5_m2_m6:C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O, amount is: 0.0 ;m1_m5_m2_m6:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m7:CN(C)C=O, amount is: 0.0 ;m1_m5_m2_m6:CN(C)C=O, amount is: 0.0 ;m1_m5_m2_m6:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (4.76 g, 20 mmol) in 50 mL DMF was added to a suspension of NaH (0.8 g, 20 mmol) in 25 mL DMF. The suspension was stirred at ambient temperatures for 30 minutes, then heated to 50° C. for 30 minutes. A solution of methyl 3-bromomethylbenzoate (2.86 g, 12.5 mmol) in 20 mL DMF was then added and the reaction stirred for 10 min at 50° C. The mixture was poured into 1N HCl, filtered, washed with water and dried. Chromatography on silica gel (2% EtOH in 7:3 methylene chloride/ethyl acetate) afforded 1.2 g of 3-(3-methoxycarbonylphenyl)methyl4,5-diphenyl-1H-imidazol-2-one as a white solid. |
Here is a chemical reaction formula: Reactants are m1:C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O, amount is: 0.0 MOLE;m2:BrCC1=CC=C2C=CC(=CC2=C1)C#N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(#N)C=1C=C(C=CC1)CN1C(N(C(=C1C1=CC=CC=C1)C1=CC=CC=C1)CC1=CC=C2C=CC(=CC2=C1)C#N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a manner similar to Preparation 2 above, 3-[(2,3-dihydro4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile was reacted with 7-(bromomethyl)-naphthalene-2-carbonitrile to give 7-[[3-(3-cyanophenyl)methyl-2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl]methyl]naphthalene-2-carbonitrile; NMR (CDCl3)8.05 (s,1), 7.9 (d,1), 7.85 (d,1), 7.55 (m,3), 7.4 (m,2), 7.2 (m,9), 7.0 (m,3), 5.1 (s,2), 4.95 (s,2) ppm. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(=O)[O-].[NH4+], amount is: 0.0 ;m1_m2_m3:O=C1C(CC2=CC=CC=C12)N1C(=NC(=C1)C(=O)OCC)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C1C=2N(C3=C(N1)C=1C=CC=CC1C3)C=C(N2)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 51.2 g of ammonium acetate are added in small portions to a solution of 2 g of diethyl 1-(1-oxoindan-2-yl)imidazole-2,4-dicarboxylate in 80 ml of acetic acid and the mixture is heated to reflux for 2 hours. After cooling to a temperature close to 20° C. the precipitate formed is filtered off and rinsed with distilled water and then with methyl ethyl ketone (2×10 ml) to give 0.65 g of ethyl 4,5-dihydro-4-oxo-10H-imidazol[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in the form of a beige solid melting above 260° C. (analysis % calculated C: 65.08, H: 4.44, N: 14.23; % found C: 65.2, H: 4.3, N: 13.8). |
Here is a chemical reaction formula: Reactants are m1:CN=C=O, amount is: 0.0 ;m2_m3:NC1=CC=2CC3=C(NC(C=4N3C=C(N4)C(=O)OCC)=O)C2C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CNC(NC1=CC=2CC3=C(NC(C=4N3C=C(N4)C(=O)OCC)=O)C2C=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.44 ml of methyl isocyanate is added dropwise with stirring to a suspension of 580 mg of ethyl 8-amino-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in 10 ml of dimethylformamide and stirring is continued for 12 hours at a temperature close to 20° C. The reaction mixture is then filtered, rinsed with dimethylformamide and dried at 35° C. under vacuum (1 mm Hg; 0.13 kPa). 320 mg of ethyl 8-(3-methylureido)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate are obtained as a dihydrate in the form of a beige solid melting above 260° C. (analysis % calculated C: 53.59, H: 5.25, N: 17.36; % found C: 53.2, H: 4.7, N: 17.7). |
Here is a chemical reaction formula: Reactants are m3:C(C)(=O)O, amount is: 0.0 ;m1:ClC1=CC=C2CC(C(C2=C1)=O)N1C(=NC(=C1)C(=O)OCC)C(=O)OCC, amount is: 0.0 ;m2:C(C)(=O)[O-].[NH4+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m6_m0:CO, amount is: 0.0 MOLE;m5_m6_m0:CC(=O)C, amount is: 0.0 MOLE;m4:C(C)#N, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1C=CC=2CC3=C(NC(C=4N3C=C(N4)C(=O)OCC)=O)C2C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The procedure is as in Example 1 but starting from 5 g of diethyl 1-(6-chloro-1-oxoindan-2-yl)imidazole-2,4-dicarboxylate, 118 g of ammonium acetate and 190 ml of acetic acid. After washing the precipitate with water and then with methyl ethyl ketone, the solid obtained is first of all ground in acetonitrile and then in methanol and finally in acetone to obtain 2.7 g of ethyl 7-chloro-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in the form of a brown solid melting above 260° C. (analysis % calculated C: 58.28, H: 3.67, Cl: 10.75, N: 12.74; % found C: 58.6, H: 3.4, Cl: 10.4, N: 13.1). |
Here is a chemical reaction formula: Reactants are m1_m2_m5:[H-].[Na+], amount is: 0.0 ;m1_m2_m5:O=C1C=2N(C3=C(N1)C=1C=CC=CC1C3)C=C(N2)C(=O)OCC, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE;m3:N(=O)OCCC(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:CS(=O)C, amount is: 0.0 ;m6:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ON=C1C=2C=CC=CC2C=2NC(C=3N(C21)C=C(N3)C(=O)O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.34 g of sodium hydride is added to 1 g of ethyl 4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in solution in 20 ml of anhydrous dimethyl sulphoxide, while the temperature of the reaction mixture is maintained below 20° C. 0.44 ml of isoamyl nitrite is then added and stirring is continued for 18 hours at the same temperature. The reaction mixture is then poured into iced water and the solution is acidified with 15 ml of acetic acid. The precipitate formed is filtered off, washed with water, with acetone and then with methanol and finally dried under reduced pressure (1 mm Hg; 0.13 kPa) to produce 0.25 g of 10-hydroxyimino-4,5-dihydro-4-oxo-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylic acid in the form of a brown powder whose melting point is higher than 260° C. (1H spectrum in DMSO, T=300K, δ in ppm (200 MHz), mixture of the syn and anti isomers: Major isomer: between 7.30 and 7.50 (2H, m, CH arom.), 7.62 (1H, s, CH arom.), 7.82 (1H, d, J=7 Hz, CH arom.), 8.00 (1H, s, CH arom.), 8.20 (1H, d, J=7 Hz, CH arom.), 12.7 (1H, s, NH), 13.0 (1H, s, OH), Minor isomer: between 7.30 and 7.50 (2H, m, CH arom.), 7.51 (1H, s, CH arom.), 7.70 (1H, d, J=7 Hz, CH arom.), 7.88 (1H, d, J=7 Hz, CH arom.), 8.58 (1H, s, CH arom.), 12.7 (1H, s, NH), 13.2 (1H, s, OH)). |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)N1C(C=2N(C3=C1C=1C=CC=CC1C3)C(=C(N2)C(=O)[O-])Cl)=O, amount is: 0.0 ;m1_m2:Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC=1C=CC=2CC3=C(NC(C=4N3C=C(N4)C(=O)O)=O)C2C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.58 g of ethyl-chloro-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in suspension in 10 ml of 6N hydrochloric acid is heated to reflux for 24 hours. After cooling to a temperature close to 20° C., the insoluble matter is filtered off, washed with water and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 45° C. 0.38 g of 7-chloro-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]-pyrazine-2-carboxylic acid is thus obtained in the form of a beige powder whose melting point is higher than 260° C. (analysis C14H10ClN3 O4 ; % calculated C: 52.60, H: 3.15, Cl: 11.09, N: 13.14; % found C: 52.9, H: 3.3, Cl: 10.8, N: 12.9); 1H spectrum in DMSO, T=300K, δ in ppm (300 MHz): 4.02 (2H, s, CH2), 7.37 (1H, d, J=7 Hz, CH arom.), 7.60 (1H, d, J=7 Hz, CH arom.), 7.92 (1H, s, CH arom.), 8.52 (1H, s, CH arom.), 12.45 (1H, s, NH)). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:[OH-].[Na+], amount is: 0.0 ;m1_m2_m3:O=C1C=2N(C3=C(N1)C=1C=CC=CC1C3)C=C(N2)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:O1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C1C=2N(C3=C(N1)C=1C=CC=CC1C3=O)C=C(N2)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5 ml of 1N sodium hydroxide are added to a suspension of 0.2 g of ethyl 4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in 15 ml of dioxane, and the reaction mixture is stirred vigorously while compressed air is bubbled for 15 hours. After addition of 10 ml of distilled water the mixture is acidified with concentrated hydrochloric acid. The precipitate form is filtered off, washed with water and dried to produce 0.13 g of 4,5-dihydro-4,10-dioxoimidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylic acid in the form of a brown powder whose melting point is higher than 260° C. (1H spectrum in DMSO, T=300K, δ in ppm (200 MHz): between 7.35 and 7.65 (3H, m, CH arom. ), 7.75 (1H, d, J=7 Hz, CH arom.), 8.38 (1H, s, CH arom.), 12.5 (1H, s, NH)). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:N1=CC=C(C=C1)COC1=CC=C2CCCC(C2=C1)=O, amount is: 0.0 ;m1_m2_m3:C(C1=CC=CC=C1)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)NC1CCCC2=CC=C(C=C12)OCC1=CC=NC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of Compound 1 (820 mg, 3.24 mmol) and benzyl amine (354 μL, 3.24 mmol) in benzene (10 mL) was heated to reflux under azeotropic conditions. After the calculated amount of water was collected, the reaction was cooled and concentrated in vacuo. The residue was taken-up into ethanol (5 mL) and added to a slurry of sodium boroydride (246 mg, 6.48 mmol) in ethanol (15 mL). The reaction was heated to 80° C., stirred for 30 min, cooled and concentrated in vacuo. The residue was diluted with ethyl acetate followed by the slow addition of 1N hydrochloric acid. The layers were separated. The aqueous phase was adjusted to pH 7 with 2N sodium hydroxide and extracted with methylene chloride (2×). The organics were combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel (elution with 5% methanol:methylene chloride) provided 1.09 g of Compound 12 as an oil. |
Here is a chemical reaction formula: Reactants are m1_m3:CC=1C(=C2CCC(C(C2=CC1OCCC)=O)=CC=1C=NC=CC1)OCCC, amount is: 0.0 ;m2:[H][H], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:CO, amount is: 0.0 ,Catalysts are m1_m3:[Pd], amount is: 0.0 .Products are 0:CC=1C(=C2CCC(C(C2=CC1OCCC)=O)CC=1C=NC=CC1)OCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of Compound 25 (3.96 g, 10.8 mmol) and 10% palladium on carbon (600 mg) in abs. methanol (100 mL) was hydrogenated at 1 atm for 12 hr. The hydrogen was replaced with nitrogen, the reaction was filtered and concentrated in vacuo. Chromatography of the residue on silica gel (elution with 20% ethyl acetate:hexanes) provided 2.72 g of Compound 26. |
Here is a chemical reaction formula: Reactants are m1_m2:N1C[C@H](C(=O)OCC)CCC1, amount is: 0.0 ;m1_m2:N, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:N1C[C@H](C(=O)N)CCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 14.7 g (93.5 mmol) of (R)-ethyl nipecotate in a 300 ml round-bottomed flask were added 200 ml of concentrated aqueous ammonia at room temperature, and the mixture was allowed to stand for 3 days at room temperature. The reaction mixture was distilled off at a water bath temperature of lower than 40° C. to obtain (R)-nipecotamide as a pale yellow oil. To this were added 100 ml of methylene chloride and 50 ml of ethanol at room temperature, and 15.6 ml (1.2 eg.) of triethylamine were added while cooling with ice. To this reaction mixture were gradually added dropwise 11.1 ml (1 eg.) of benzyl bromide under cooling with ice. After dropwise addition, the mixture was stirred for 10 minutes under cooling with ice and further for 4 hours after returned to room temperature, which was allowed to stand overnight. The reaction mixture was distilled off under reduced pressure and the residue obtained was dissolved into 200 ml of methylene chloride, which was washed with 1N sodium hydroxide and saturated aqueous solution of sodium chloride in turn. The aqueous layer was extracted with methylene chloride (50 ml×3) and, after washed with saturated aqueous solution of sodium chloride, these were combined with previous organic layer and dried over anhydrous sodium sulfate. Solvent was distilled off under reduced pressure and the residue thus obtained was recrystallized to obtain 8.61 g (yield 42 %) of title compound. |
Here is a chemical reaction formula: Reactants are m5_m6:O1CCCC1, amount is: 0.0 ;m5_m6:COCC(=O)Cl, amount is: 0.0 ;m1_m2_m3_m4:O1CCCC1, amount is: 0.0 ;m1_m2_m3_m4:C1(=CC=CC=C1)CN1C[C@@H](CCC1)N, amount is: 0.0 ;m1_m2_m3_m4:O1CCCC1, amount is: 0.0 ;m1_m2_m3_m4:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m8_m7:O, amount is: 0.0 MOLE;m8_m7:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:COCC(=O)N[C@H]1CN(CCC1)CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a 50 ml anhydrous tetrahydrofuran solution of 5.00 g (26.3 mmol) of (R)-1-phenylmethyl-3-aminopiperidine (Referential example 7) in a 300 ml three-necked flask was added a 50 ml anhydrous tetrahydrofuran solution of 3.20 g (1.2 eg.) of triethylamine, and, to this reaction mixture was added dropwise a 50 ml anhydrous tetrahydrofuran solution of 2.85 g (1.0 eg.) of methoxyacetyl chloride under stirring and cooling with ice. After reacted for 5 hours at room temperature, methylene chloride and small amount of water were added to extract (20 ml×6). The organic layers were combined and dried over anhydrous sodium sulfate. Then, solvent was distilled off under reduced pressure and the residue thus obtained was purified by column chromatography (alumina, ethyl acetate:n-hexane=1:1) to obtain 6.67 g (yield 97 %) of title compound as a pale yellow oil. |
Here is a chemical reaction formula: Reactants are m3_m5:ClC(=O)N1C2=CC=CC=C2C2CCCCC12, amount is: 0.0 ;m3_m5:C1CCOC1, amount is: 0.0 ;m1_m4:C(CCC)N1CCC(CC1)CO, amount is: 0.0 ;m1_m4:C1CCOC1, amount is: 0.0 ;m2:C[Li], 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(=O)(O)N1C2=CC=CC=C2C2CCCC(C12)CC1CCN(CC1)CCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-Butyl-4-piperidinylmethanol (0.500 g 2.12 mmol) was dissolved in dry THF (3 ml) and treated with methyllithium (1.5M solution in diethyl ether) 2.16 ml, 2.33 mmol) with stirring under nitrogen. After 10 minutes, N-chlorocarbonyl-1,2,3,4,4a,9a-hexahydrocarbazole (0.630 g, 2.68 mmol) (Ref: WO 89/09217) in dry THF (5 ml) was added dropwise with stirring. After 48 hours, the reaction mixture was filtered and the filtrate evaporated under reduced pressure. The residue was purified by silica-gel chromatography, eluting with 2% MeOH/CHCl3 -3%MeOH/CHCl3 to give the title compound as a clear, colourless oil, which was converted to the oxalate salt, nap 187°-189° C. |
Here is a chemical reaction formula: Reactants are m1_m4:C(=O)(O)N1C2=CC=CC=C2C2CCCC(C12)CC1CCN(CC1)CCCC, amount is: 0.0 ;m3:ClC=1C(C(=C(C(C1Cl)=O)C#N)C#N)=O, amount is: 0.0 ;m2:ClC=1C(C(=C(C(C1Cl)=O)C#N)C#N)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)N1C2=CC=CC=C2C=2C=CC=C(C12)CC1CCN(CC1)CCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-Carboxy-[1-butylpiperidin-4-ylmethyl]-1,2,3,4,4a,9a-hexahydrocarbazole (0.530 g, 1.32 mmol) was dissolved in chloroform (25 ml) and treated with 2,3-dichloro-5,6-dicyano-1, 4-benzoquinone (0.329 g, 1.58 mmol) with stirring. The mixture was heated to reflux for 12 hours, cooled, and more 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.329 g 1.58 mmol) added with stirring. The mixture was heated to reflux for 12 hours, cooled and evaporated under reduced pressure. The residue was purified by Silica-gel chromatography, eluting with 2%MeOH/CHCl3 to give the title compounds as 3:1 mixture. The mixture was separated by preparative HPLC using a Waters Micro Bondapak C18 (300 mm×7.8 mm) column and eluting with 75:25 MeCN: 0.1M Ammonium Acetate (pH 5.0). |
Here is a chemical reaction formula: Reactants are m1_m4:COC(=O)C1=CC2=CC=CC=C2C=C1O, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 MOLE;m3:C(C#C)Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(=O)C1=CC2=CC=CC=C2C=C1OCC#C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl-3-hydroxy-2-naphthoate (2.63 g, 0.013 mol) was dissolved in dry THF (80 ml) and treated with sodium hydride (80%) ((0.398 g, 0.013 mol), with stirring under N2. After 0.5 h, propargyl bromide (80% in toluene) (2.57 ml 0.017 mol) was added and the mixture heated to reflux. After 20 h, the reaction mixture was allowed to cool and then evaporated under reduced pressure. The residue was then evaporated under reduced pressure. The residue was then partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (1×), and the combined organic layers were dried (Na2SO4) and evaporated to given an orange oil. Crystallisation of the oil from petrol (60/80) diethyl ether provided the title compound as a pale yellow solid (1.0 gg, 35%). |
Here is a chemical reaction formula: Reactants are m1:[N+](=O)([O-])C=1C=C(C=CC1)S(=O)(=O)NC1=CC=2C(=NSN2)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2:CO, amount is: 0.0 ,Catalysts are m3:[Ni], amount is: 0.0 .Products are 0:NC=1C=C(C=CC1)S(=O)(=O)NC1=CC=2C(=NSN2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1 g of 3-nitro-N-(2,1,3-benzothiadiazol-5-yl)-1-benzenesulfonamide in 25 ml of methanol is hydrogenated to completion on 1 g of Raney Nickel at normal pressure and 20°. The solution is filtered, evaporated and 3-amino-N-(2,1,3-benzothiadiazol-5-yl)-1-benzenesulfonamide is obtained. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=2C(=NON2)C=C1, amount is: 0.0 MOLE;m1_m2:C(C)C1=C(C=CC=C1)S(=O)(=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(C)C1=C(C=CC=C1)S(=O)(=O)NC1=CC=2C(=NON2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Analogously to Example 1, by reaction of 5-amino-2,1,3-benzoxadiazole (obtainable by reduction of 5-nitro-2,1,3-benzoxadiazole-1- or 3-N-oxide with triethyl phosphite) with 2-ethylbenzenesulfonyl chloride, 2-ethyl-N-(2,1,3-benzoxadiazol-5-yl)-1-benzenesulfonamide is obtained. |
Here is a chemical reaction formula: Reactants are m1_m2:CN(C1=C2C=CC=C(C2=CC=C1)S(=O)(=O)NC1=C(C(=CC2=NON=C21)CC)Br)C, amount is: 0.0 ;m1_m2:[Cu](C#N)C#N, amount is: 0.0 ;m3:N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C1=C2C=CC=C(C2=CC=C1)S(=O)(=O)NC1=C(C(=CC2=NON=C21)CC)C#N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4.6 g of 5-dimethylamino-N-(5-bromo-6-ethyl-2,1,3-benzoxadiazol-4-yl)-1-naphthalenesulfonamide and 1.3 g of copper cyanide is heated for 8 hours at 120° in 30 ml of pyridine. The mixture is poured onto aqueous ammonia solution, worked up in the customary manner and 5-dimethylamino- N-(5-cyano-6-ethyl-2,1,3-benzoxadiazol-4-yl)-1-naphthalenesulfonamide is obtained. |
Here is a chemical reaction formula: Reactants are m1:CN(C1=C2C=CC=C(C2=CC=C1)S(=O)(=O)NC1=C(C(=CC2=NON=C21)CC)C#N)C, amount is: 0.0 ;m2:[OH-].[K+], amount is: 0.0 ;m3:C(C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C1=C2C=CC=C(C2=CC=C1)S(=O)(=O)NC1=C(C(=CC2=NON=C21)CC)C(=O)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1 g of 5-dimethylamino-N-(5-cyano-6-ethyl-2,1,3-benzoxadiazol-4-yl)-1-naphthalenesulfonamide and 0.7 g of potassium hydroxide in 20 ml of ethanol and 5 ml of water is bailed with stirring for 8 hours. The solvents are removed, the residue is dissolved in water and treated with hydrochloric acid and 5-dimethylamino-N-(5-carboxy-6-ethyl-2,1,3-benzoxadiazol-4-yl)-1-naphthalenesulfonamide is obtained. |
Here is a chemical reaction formula: Reactants are m1_m6_m5_m2:NC1=CC=C(C=C1)S(=O)(=O)NC1=CC=2C(=NSN2)C=C1, amount is: 0.0 ;m1_m6_m5_m2:C(C)=O, amount is: 0.0 MOLE;m4:Cl, amount is: 0.0 MOLE;m3:C(#N)[BH3-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6_m5_m2:CO, amount is: 0.0 ,Catalysts are m1_m6_m5_m2:[Ti](Cl)(Cl)(Cl)Cl, amount is: 0.0 .Products are 0:C(C)NC1=CC=C(C=C1)S(=O)(=O)NC1=CC=2C(=NSN2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 6 g of 4-amino-N-(2,1,3-benzothiadiazol-5-yl)-1-benzenesulfonamide and 0.5 g of titanium tetrachloride in 100 ml of methanol is treated with 1 ml of freshly distilled acetaldehyde. 4 g of sodium cyanoborohydride are then added thereto and the mixture is stirred for 30 hours. Cold half-concentrated hydrochloric acid is added thereto, the mixture is worked up in the customary manner and 4-ethylamino-N-(2,1,3-benzothiadiazol-5-yl)-1-benzenesulfonamide is obtained. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:O(C1=CC=CC=C1)C1=CC=C(C#N)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(CCC)[Sn](CCCC)=O, amount is: 0.0 ;m1_m2_m3_m4:C[Si](C)(C)N=[N+]=[N-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O(C1=CC=CC=C1)C1=CC=C(C=C1)C1=NN=NN1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 4-phenoxybenzonitrile (9.87 g), dibutyltin oxide (3.88 g), and trimethylsilyl azide (33.5 ml) in anhydrous toluene (200 ml) was heated to reflux for 6 hours. The reaction mixture was washed with 1.6M sodium hydroxide (2×250 ml). The combined aqueous layer was washed with diethyl ether (4×120 ml) then acidified to pH 6 with concentrated hydrochloric acid. The acidic solution was washed with ethyl acetate (3×200 ml) and the combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to dryness to give 5-(4-phenoxyphenyl)-1H-tetrazole as a white powder. |
Here is a chemical reaction formula: Reactants are m7_m4:[Cl-].[Na+], amount is: 0.0 ;m1_m2_m6_m5_m3:C(#C)C1=CC=C(C#N)C=C1, amount is: 0.0 ;m1_m2_m6_m5_m3:BrC=1SC(=CC1)[N+](=O)[O-], amount is: 0.0 ;m1_m2_m6_m5_m3:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7_m4:C(C)(=O)OCC, amount is: 0.0 ;m1_m2_m6_m5_m3:CN(C=O)C, amount is: 0.0 ,Catalysts are m1_m2_m6_m5_m3:Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl, amount is: 0.0 .Products are 0:[N+](=O)([O-])C1=CC=C(S1)C#CC1=CC=C(C#N)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-ethynylbenzonitrile (0.5 g), 2-bromo-5-nitrothiophene (0.9 g) and bis(triphenylphosphine)palladium dichloride (83 mg) in anhydrous dimethylformamide (4 ml) was added triethylamine (2.2 ml). The reaction mixture was stirred at room temperature for 3 days then ethyl acetate (200 ml) and saturated sodium chloride (200 ml) were added. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The crude solid was triturated with 1:1 dichloromethane/hexane followed by diethyl ether to give 4-[(5-nitro-2-thienyl)ethynyl]benzonitrile as a yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:[N+](=O)([O-])C1=CC=C(S1)C#CC1=CC=C(C#N)C=C1, amount is: 0.0 ;m1_m2_m4_m3:C(CCC)[Sn](CCCC)=O, amount is: 0.0 ;m1_m2_m4_m3:C[Si](C)(C)N=[N+]=[N-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(S1)C#CC1=CC=C(C=C1)C1=NN=NN1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-[(5-nitro-2-thienyl)ethynyl]benzonitrile (0.6 g) and dibutyltin oxide (59 mg) in anhydrous toluene (30 ml) was added trimethylsilyl azide (0.5 ml). The reaction mixture was heated to reflux in the dark for 12 hours, then allowed to cool to room temperature. The reaction mixture was washed with saturated sodium bicarbonate (2×300 ml) and the combined aqueous layer was acidified to pH 1 with concentrated hydrochloric acid (30 ml). The acidified solution was washed with 1:1 ethyl acetate/tetrahydrofuran (500 ml) and the organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to dryness to give 5-[4-[(5-nitro-2-thienyl)ethynyl]-phenyl]-1H-tetrazole as a yellow solid. |
Here is a chemical reaction formula: Reactants are m4:[OH-].[Na+], amount is: 0.0 ;m1_m5_m2_m3:O(C1=CC=CC=C1)C1=CC=C(C=C1)CC#N, amount is: 0.0 ;m1_m5_m2_m3:C[Si](C)(C)N=[N+]=[N-], amount is: 0.0 ;m1_m5_m2_m3:C(CCC)[Sn](CCCC)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m3:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O(C1=CC=CC=C1)C1=CC=C(C=C1)CC1=NN=NN1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-phenoxyphenylacetonitrile (1.16 g) in anhydrous toluene (30 ml) was added trimethylsilylazide (1.1 ml) and dibutyltin oxide (0.19 g). The mixture was heated to reflux for 19 hours then allowed to cool to room temperature. The reaction mixture was then added to 1M sodium hydroxide (100 ml) and washed with diethyl ether (3×50 ml). The aqueous layer was acidified with concentrated hydrochloric acid (30 ml) then washed with 5:1 ethyl acetate/tetrahydrofuran (60 ml) and ethyl acetate (2×50 ml). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to give 5-(4-phenoxyphenylmethyl)-1H-tetrazole as a white solid. |
Here is a chemical reaction formula: Reactants are m2:Cl, amount is: 0.0 ;m1_m3:ClC=1C=C2C(C(=O)NC2=O)=CC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C2CNCC2=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-chlorophthalimide (60 g) in 1 liter of tetrahydrofuran was added borane-methyl sulfide complex (100 ml of 10M), and the mixture was refluxed overnight. After cooling, 100 ml of 6N hydrochloric acid was added slowly, the mixture refluxed for 2 hours, and then filtered. The filtrate was concentrated under reduced pressure, and the resulting aqueous solution washed with ethyl acetate. The aqueous layer was then basified with ammonium hydroxide and extracted with methylene chloride. Solvent was removed from the extract, and the residue distilled under vacuum to give 4-chloroisoindoline, a white solid, m.p. 48°-50° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC1=C2CNCC2=CC=C1, amount is: 0.0 ;m1_m2_m3:CSC=1SCCN1, amount is: 0.0 ;m1_m2_m3:C1=C(C=CC2=CC=CC=C12)S(=O)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=C2CN(CC2=CC=C1)C=1SCCN1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-chloroisoindoline (700 mg), 2-methylthio-2-thiazoline (600 mg), and β-naphthylsulfonic acid (35 mg) was heated at 150° C. for 30 minutes. The product was cooled, dissolved in methylene chloride, washed with water, the organic layer dried over anhydrous potassium carbonate, filtered, and solvent removed from the filtrate under reduced pressure. The residue was chromatographed on silica gel packed in methylene chloride/2% methanol/ammonia, eluting with methylene chloride/2% methanol, to give 4-chloro-2-(thiazolin-2-yl)isoindoline, a compound of Formula (IA), m.p. 167°-169° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC1=C2CNCC2=CC=C1, amount is: 0.0 ;m1_m2_m3_m4:C(C)OC=1OCCN1, amount is: 0.0 ;m1_m2_m3_m4:C1=C(C=CC2=CC=CC=C12)S(=O)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=C2CN(CC2=CC=C1)C=1OCCN1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-fluoroisoindoline (400 mg), 2-ethoxy-2-oxazoline (400 mg), and β-naphthylsulfonic acid (30 mg) in 50 ml of toluene was stirred at 100° C. for 1 hour. The solvent as removed under reduced pressure, and the residue chromatographed on silica gel, eluting with 1-4% methanol in ethyl acetate, to give 4-fluoro-2-(oxazolin-2-yl)isoindoline, a compound of Formula (IB), m.p. 125°-129° C. |
Here is a chemical reaction formula: Reactants are m2_m5:OC1=NC=C(C(=O)OCC2=CC=CC=C2)C=C1, amount is: 0.0 ;m3:C1(CCCCC1)N=C=NC1CCCCC1, amount is: 0.0 ;m1_m4:C(CCCCC)C=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m5:C(Cl)Cl, amount is: 0.0 ;m1_m4:C(Cl)Cl, amount is: 0.0 ,Catalysts are m6:CN(C1=CC=NC=C1)C, amount is: 0.0 .Products are 0:C(CCCCC)C=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C(=O)OC1=NC=C(C(=O)OCC2=CC=CC=C2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 6 g of 3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carboxylic acid were dissolved in 180 ml of methylene chloride. After the addition of a solution of 4.8 g of benzyl 6-hydroxy-nicotinate in 160 ml of methylene chloride and of 2.3 g of 4-dimethylaminopyridine, the solution was cooled to 0° C. and treated with 4.4 g of dicyclohexylcarbodiimide. The reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 2 hours, thereafter poured into ice-cold aqueous ammonium chloride solution, extracted several times with ether, washed with water, dried over sodium sulfate and evaporated. The crude product, for the most part crystalline, was filtered over silica gel (eluent hexane/ethyl acetate=9:1) and recrystallized from hexane. After repeated crystallization of the mother liquor there were obtained all together 5.7 g of benzyl 6-(3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carbonyloxy)-nicotinate in colorless crystals, m.p. 94°-95° C. |
Here is a chemical reaction formula: Reactants are m1_m2:C(#CCCCC)C=1C=CC2=C(C(CCCC2)(C)C)C1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2:C(C)(=O)OCC, amount is: 0.0 ,Catalysts are m3:[Pd], amount is: 0.0 .Products are 0:C(CCCCC)C=1C=CC2=C(C(CCCC2)(C)C)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: This alkyne was dissolved in 30 ml of ethy acetate and hydrogenated over 2 g of Pd/C (10%) at room temperature and under 1 atm H2. Filtration over diatomaceous earth and removal of the solvent gave 3.08 g of 2-hexyl-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene as a colorless oil (GC purity: 98%). |
Here is a chemical reaction formula: Reactants are m2_m4:BrBr, amount is: 0.0 ;m1_m3:C(CCCCC)C=1C=CC2=C(C(CCCC2)(C)C)C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m4:C(Cl)Cl, amount is: 0.0 ;m1_m3:C(Cl)Cl, amount is: 0.0 ,Catalysts are m5:[Fe], amount is: 0.0 MOLE.Products are 0:BrC=1C(=CC2=C(CCCCC2(C)C)C1)CCCCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: This 3.08 g of 2-hexyl-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene were dissolved in 35 ml of CH2Cl2, treated at 0° with a spatula tip of Fe powder and then reacted with a solution of 0.67 ml of Br2 (1.1 eq.) in 5 ml of CH2Cl2. After 30 min., the mixture was poured on to ice, extracted with diethyl ether, washed with bisulphite solution and NaCl soln., dried over Na2SO4 and evaporated to dryness. Flash chromatography on SiO2 (hexane) gave 3.21 g of 2-bromo-3-hexyl-5,5-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene as a colorless oil (GC purity: 82%, moreover 2% ed., 2.6% regioisomer, 8.3% dibromo compound and further prod.). |