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Here is a chemical reaction formula: Reactants are m2_m7_m8:OCC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCO, amount is: 0.0 ;m1_m5_m6:[H-].[Na+], amount is: 0.0 ;m3:BrC=1C=NC(=NC1)Cl, amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m7_m8:CC(=O)N(C)C, amount is: 0.0 ;m2_m7_m8:C1CCOC1, amount is: 0.0 ;m1_m5_m6:CC(=O)N(C)C, amount is: 0.0 ;m1_m5_m6:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C=NC(=NC1)OCC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of sodium hydride (65 mg) in dimethylacetamide (0.5 ml) and tetrahydrofuran (0.5 ml) is added dropwise a solution of 4-(2-hydroxy-1,1-dimethylethyl)-N-{6-[2-hydroxyethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (135 mg) in dimethylacetamide (2 ml) and THF (2 ml) solution over period of 5 minutes at room temperature, and thereto is added 5-bromo-2-chloropyrimidine (399 mg). The mixture is stirred at room temperature for 6 days. The reaction mixture is acidified with cold diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer is washed with water and saturated brine, dried over anhydrous sodium sulfate, and evaporated to remove the solvent. The oily residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=100:1), and evaporated to remove the solvent. The resulting crude crystals are recrystallized from methylene chloride/isopropyl ether to give 4-[2-(5-bromopyrimidin-2-yloxy)-1,1-dimethylethyl]-N-{6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (77 mg) as colorless crystals. |
Here is a chemical reaction formula: Reactants are m1_m5_m2_m3:C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)O, amount is: 0.0 ;m1_m5_m2_m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m5_m2_m3:BrC=1C=NC(=NC1)Cl, amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m2_m3:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)OC1=NC=C(C=N1)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-tert-butyl-N-{6-[2-(5-hydroxypyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (200 mg) in dimethylformamide (4 ml)is added potassium carbonate (154 mg), 5-bromo-2-chloropyrimidine (216 mg), and the mixture is stirred at 50° C. for two hours. The reaction mixture is acdified with cold hydrochloric acid, and extracted with ethyl acetate. The organic layer is washed with water and brine, and dried over anhydrous sodium sulfate, and evaporated to remove the solvent. The oily residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=50:1), and the fractions are evaporated to remove the solvent. The resulting crude crystals are recrystallized from methylene chloride/isopropyl ether to give 4-tert-butyl-N-{6-[2-(5-(5-bromopyrimidin-2-yloxy)pyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (238 mg) as colorless needles. |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 MOLE;m1_m2:C(CCO)O, amount is: 0.0 ;m1_m2:[H-].[Na+], amount is: 0.0 ;m3:C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)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:C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 1,3-propanediol (7 ml) is added sodium hydride (60% dispersion-type, 312 mg), and thereto is added 4-tert-butyl-N-{6-chloro-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide (707 mg). The reaction mixture is reacted at 90° C. for two hours, and then reacted at 130° C. for one hour. The reaction solution is acidified with 10% hydrochloric acid, and extracted with ethyl acetate, and the ethyl acetate layer is washed, dried, and concentrated to dryness under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1), and crystallized from ethyl acetate/diisopropyl ether to give 4-tert-butyl-N-{6-(3-hydroxypropyloxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide (315 mg) as crystals. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC1=C(C(=NC=N1)OCCO)C1=CC=C(C=C1)C, amount is: 0.0 ;m1_m2_m3:[N-]=[N+]=[N-].[Na+], amount is: 0.0 ;m1_m2_m3:CN(C=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:N(=[N+]=[N-])C1=C(C(=NC=N1)OCCO)C1=CC=C(C=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-{6-chloro-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol (21.85 g), sodium azide (10.7 g) and dimethyformamide (260 ml) is heated with stirring at 75°-80° C. overnight. After cooling, the mixture is treated with water, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is crystallized from hexane to give 2-{6-azido-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol (19.6 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:N(=[N+]=[N-])C1=C(C(=NC=N1)OCCO)C1=CC=C(C=C1)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,Catalysts are m1_m2_m3:[C].[Pd], amount is: 0.0 .Products are 0:NC1=C(C(=NC=N1)OCCO)C1=CC=C(C=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-{6-azido-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol (19.6 g), 10% palladium-carbon (50% moist) (4.0 g) and ethanol (240 ml) is subjected to catalytic hydrogenation at room temperature under hydrogen atmosphere (1 atm) for one hour. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is recrystallized from ethyl acetate/n-hexane to give 2-{6-amino-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol (15.9 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=NC=NC(=C1C1=CC=C(C=C1)C)Cl, amount is: 0.0 ;m1_m3_m2:N.C(C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CCOCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C(=NC=N1)N)C1=CC=C(C=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4,6-dichloro-5-(4-methylphenyl)pyrimidine (4.14 g) in ether (20 ml) is added 27% ammonia-ethanol solution (30 ml), and the reaction mixture is reacted at room temperature in a sealed tube for three days. The mixture is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate=(10:1)~ethyl acetate) to give 6-chloro-5-(4-methylphenyl)pyrimidin-4-amine (1.89 g). |
Here is a chemical reaction formula: Reactants are m1_m4_m2:ClC1=C(C(=NC=N1)N)C1=CC=C(C=C1)C, amount is: 0.0 ;m1_m4_m2:[H-].[Na+], amount is: 0.0 ;m1_m4_m2:C(CO)O, amount is: 0.0 ;m3:[Cl-].[NH4+], 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:NC1=C(C(=NC=N1)OCCO)C1=CC=C(C=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 6-chloro-5-(4-methylphenyl)pyrimidin-4-amine (500 mg), ethylene glycol (10 ml) and sodium hydride (60% dispersion-type, 0.46 g) is reacted at 70° C. for two hours, and reacted at 90° C. for five hours. The mixture is treated with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is crystallized from hexane/ethyl acetate to give 2-{6-amino-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol (422 mg). |
Here is a chemical reaction formula: Reactants are m3:BrC=1C=NC(=NC1)Cl, amount is: 0.0 ;m4:[Cl-].[NH4+], amount is: 0.0 MOLE;m1_m5_m2:NC1=C(C(=NC=N1)OCCO)C1=CC=C(C=C1)C, amount is: 0.0 ;m1_m5_m2:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)N)C1=CC=C(C=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-{6-amino-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol (7.54 g) in tetrahydrofuran (150 ml) is added sodium hydride (60% dispersion-type, 1.47 g), and thereto is added 5-bromo-2-chloropyrimidine (7.73 g), and the mixture is stirred at room temperature overnight. To the reaction solution is added saturated aqueous ammonium chloride solution, and the mixture is evaporated to remove the solvent. The precipitated crystals are collected by filtration, washed and dried. The crude crystals are purified by silica gel column chromatography (solvent; chloroform/methanol=100:1~80:1), and recrystallized from tetrahydrofuran/diethyl ether to give 6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine (11.27 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:ClC1=NC=NC(=C1)Cl, amount is: 0.0 ;m1_m2_m4_m3:C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)N, amount is: 0.0 ;m1_m2_m4_m3:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m6:Cl, amount is: 0.0 MOLE;m5_m6:O, amount is: 0.0 MOLE;m1_m2_m4_m3:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4,6-dichloropyrimidine (1.33 g) and 4-tert-butylbenzenesulfonamide (1.96 g) in dimethylformamide (20 ml) is added sodium hydride (60% dispersion-type, 714 mg). The mixture is stirred at room temperature for two hours, and the reaction solution is diluted with 10% hydrochloric acid and water. The mixture is extracted with ethyl acetate, and the ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is recrystallized from ethyl acetate to give 4-tert-butyl-N-(6-chloropyrimidin-4-yl)benzenesulfonamide (2.02 g). |
Here is a chemical reaction formula: Reactants are m4_m1:[H-].[Na+], amount is: 0.0 ;m4_m1:C(CO)O, amount is: 0.0 ;m3:Cl, amount is: 0.0 MOLE;m2:C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1)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:C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1)OCCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To ethylene glycol (20 ml) is added sodium hydride (60% dispersion-type, 1.03 g), and thereto is added 4-tert-butyl-N-(6-chloropyrimidin-4-yl)benzenesulfonamide (1.66 g). The mixture is stirred at 60° C. for 20 hours. After cooling, the mixture is acidified with 10% hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is crystallized from ethyl acetate to give 4-tert-butyl-N-{6-(2-hydroxyethoxy)pyrimidin-4-yl}benzenesulfonamide (1.58 g). |
Here is a chemical reaction formula: Reactants are m1_m4_m2:C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1)OCCO, amount is: 0.0 ;m1_m4_m2:BrN1C(CCC1=O)=O, amount is: 0.0 ;m3:S(=O)(O)[O-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4_m2:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C(=NC=NC1OCCO)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-tert-butyl-N-[6-(2-hydroxyethoxy)pyrimidin-4-yl)benzenesulfonamide (210 mg) in dimethylformamide (4 ml) is added N-bromosuccinimide (116 mg), and the mixture is stirred at room temperature for one hour. The mixture is treated with aqueous sodium hydrogen sulfite solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1), and recrystallized from hexane/ethyl acetate to give N-[5-bromo-6-(2-hydroxyethoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (169 mg). |
Here is a chemical reaction formula: Reactants are m1_m6_m2:BrC=1C(=NC=NC1OCCO)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C, amount is: 0.0 ;m1_m6_m2:[H-].[Na+], amount is: 0.0 ;m4_m5:Cl, amount is: 0.0 MOLE;m4_m5:[Cl-].[NH4+], amount is: 0.0 MOLE;m3:ClC1=NC=C(C=N1)SC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6_m2:CC(=O)N(C)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C(=NC=NC1OCCOC1=NC=C(C=N1)SC)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of N-[5-bromo-6-(2-hydroxyethoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (3.10 g) in dimethylacetamide (30 ml) is added sodium hydride (60% dispersion-type, 720 mg), and the mixture is stirred at room temperature for 30 minutes. To the mixture is added 2-chloro-5-methylthiopyrimidine (1.51 g), and the mixture is stirred at room temperature overnight. The reaction solution is treated with 10% hydrochloric acid and saturated ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1), and recrystallized from hexane/ethyl acetate to give N-{5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide (3.34 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m4:ClC1=NC=NC(=C1)Cl, amount is: 0.0 ;m1_m2_m4:C(CO)O, amount is: 0.0 ;m3:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC(=NC=N1)OCCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 4,6-dichloropyrimidine (5.0 g), ethylene glycol (100 ml) and tetrahydrofuran (100 ml)is added sodium hydride (60% dispersion-type, 1.34 g) under ice-cooling. The mixture is stirred at the same temperature for two hours, and evaporated to remove the solvent. The residue is extracted with ethyl acetate, and the ethyl acetate extract is dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=5:1~2:1) to give 2-(6-chloropyrimidin-4-yloxy)ethanol (5.67 g) as an oily product. |
Here is a chemical reaction formula: Reactants are m1_m4_m2:ClC1=CC(=NC=N1)OCCO, amount is: 0.0 ;m1_m4_m2:[N-]=[N+]=[N-].[Na+], amount is: 0.0 ;m3:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4_m2:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N(=[N+]=[N-])C1=CC(=NC=N1)OCCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-(6-chloropyrimidin-4-yloxy)ethanol (5.61 g) in dimethylformamide (60 ml) is added sodium azide (4.18 g), and the mixture is stirred at 70° C. for 20 hours. After cooling, the reaction solution is treated with water, and extracted with ethyl acetate. The ethyl acetate layer is dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate=1:1) to give 2-(6-azidopyrimidin-4-yloxy)ethanol (1.68 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:N(=[N+]=[N-])C1=CC(=NC=N1)OCCO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,Catalysts are m1_m2_m3:[C].[Pd], amount is: 0.0 .Products are 0:NC1=CC(=NC=N1)OCCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-(6-azidopyrimidin-4-yloxy)ethanol (1.64 g), 10% palladium-carbon (0.25 g) and ethanol (20 ml) is subjected to catalytic hydrogenation at room temperature for one hour under hydrogen atmosphere (1 atm). The catalyst is removed by filtration, and the filtrate is concentrated. The residue is recrystallized from ethanol/diethyl ether to give 2-(6-aminopyrimidin-4-yloxy)ethanol (1.11 g). |
Here is a chemical reaction formula: Reactants are m1_m3:NC1=CC(=NC=N1)OCCO, amount is: 0.0 ;m2_m4:BrBr, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:CO, amount is: 0.0 ;m2_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=C(C(=NC=N1)OCCO)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 2-(6-aminopyrimidin-4-yloxy)ethanol (400 mg) in methanol (4 ml) is added dropwise a solution of bromine (437 mg) in methanol (2 ml). The mixture is evaporated to remove the solvent, and the residue is dissolved in ethyl acetate. The mixture is treated with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate/tetrahydrofuran. The organic layer is washed, dried, and evaporated to remove the solvent to give 2-(6-amino-5-bromopyrimidin-4-yloxy)ethanol (632 mg). |
Here is a chemical reaction formula: Reactants are m3:C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)Cl, amount is: 0.0 ;m1_m5_m2:BrC=1C(=NC=NC1OCCOC1=NC=C(C=N1)SC)N, amount is: 0.0 ;m1_m5_m2:[H-].[Na+], amount is: 0.0 ;m4:[Cl-].[NH4+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m7_m6:O, amount is: 0.0 MOLE;m7_m6:N1=CC=CC=C1, amount is: 0.0 MOLE;m1_m5_m2:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C(=NC=NC1OCCOC1=NC=C(C=N1)SC)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidine-4-amine (102 mg) in tetrahydrofuran (2 ml) is added sodium hydride (60% dispersion-type, 34 mg), and thereto is added 4-tert-butylbenzenesulfonyl chloride (198 mg). The mixture is stirred at room temperature for 20 minutes, and thereto are added a drop of pyridine and water. The mixture is stirred at room temperature for 30 minutes, and neutralized with saturated aqueous ammonium chloride solution. The mixture is extracted with ethyl acetate, and the ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by preparative thin layer chromatography (solvent; chloroform/methanol=15:1), and recrystallized from hexane/ethyl acetate to give N-{5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]-pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide (135 mg). The physical properties thereof are the same as those of the compound obtained in Reference Example 16-(4). |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:C(C)OC(C(C(=O)OCC)C1=CC=C(C=C1)C)=O, amount is: 0.0 ;m1_m2_m4_m3:Cl.C(CCC)(=N)N, amount is: 0.0 ;m1_m2_m4_m3:C[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=CC=C(C=C1)C=1C(=NC(=NC1O)CCC)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of diethyl(4-methylphenyl)malonate (9.45 g) and butyramidine hydrochloride (5.00 g) in methanol (25 ml) is added 28% sodium methoxide (19.67 g) under ice-cooling, and the mixture is stirred at room temperature overnight. After the reaction is complete, the reaction solution is concentrated to the half volume thereof, and the resultant is diluted with water. The mixture is acidified with 10% hydrochloric acid, and the precipitated crystals are collected by filtration, washed, and dried to give 5-(4-methylphenyl)-4,6-dihydroxy-2-n-propylpyrimidine (5.17 g) as crystalline powder. |
Here is a chemical reaction formula: Reactants are m5:C, amount is: 0.0 MOLE;m1_m6_m2:S1C=CC=C1, amount is: 0.0 ;m1_m6_m2:C(CCC)[Li].CCCCCC, amount is: 0.0 ;m4_m8:ClC=1C(C(=C(C(C1Cl)=O)C#N)C#N)=O, amount is: 0.0 ;m3:CC1=CC=C(C=C1)C=1C(=NC=NC1Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6_m2:O1CCCC1, amount is: 0.0 ;m10_m9:O, amount is: 0.0 ;m10_m9:C(C)(=O)O, amount is: 0.0 ;m4_m8:O1CCCC1, amount is: 0.0 ;m7:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=CC=C(C=C1)C=1C(=NC(=NC1Cl)C=1SC=CC1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of thiophene (1.69 g) in anhydrous tetrahydrofuran (20 ml) is added dropwise a 1.6M n-butyl lithium/n-hexane solution (11.4 ml) at 0° C. under argon atmosphere over a period of 30 minutes. To the mixture is added dropwise and gradually a solution of 5-(4-methylphenyl)-4,6-dichloropyrimidine (4.0 g) in anhydrous tetrahydrofuran (5 ml) at -60° C. The mixture is warmed to 0° C., and stirred for 1.5 hour. After the reaction is complete, to the mixture are added acetic acid (1.5 g) and water (0.25 g), and further added thereto a solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (5.70 g) in tetrahydrofuran (5 ml), and the mixture is stirred at 0° C. for one hour. The mixture is treated with an active charcoal, and extracted with a mixture of ethyl acetate and aqueous citric acid solution. The extract is washed, dried and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=50:1) to give 5-(4-methylphenyl)-4,6-dichloro-2-(2-thienyl)pyrimidine (2.64 g) as powder. |
Here is a chemical reaction formula: Reactants are m1_m3:CC1=CC=C(C=C1)C=1C(=NC=NC1Cl)Cl, amount is: 0.0 MOLE;m2:C1(=CC=CC=C1)[Li].C1CCCCC1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CC1=CC=C(C=C1)C=1C(=NC(=NC1Cl)C1=CC=CC=C1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 5-(4-methylphenyl)-4,6-dichloropyrimidine in ether is cooled at -30° C., and thereto is added dropwise a 1.8M phenyl lithium/cyclohexane solution. The reaction mixture is treated in the same manner as in Reference Example 20-(1) to give 5-(4-methylphenyl)-4,6-dichloro-2-phenylpyrimidine as crystalline powder. |
Here is a chemical reaction formula: Reactants are m1_m2:ClC1=NC=C(C=N1)Br, amount is: 0.0 MOLE;m1_m2:O1C(=CC=C1)[Sn](CCCC)(CCCC)CCCC, 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:ClC1=NC=C(C=N1)C=1OC=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Chloro-5-bromopyrimidine and 2-furyltributyltin are treated in the same manner as in Example 190 to give 2-chloro-5-(2-furyl)pyrimidine. |
Here is a chemical reaction formula: Reactants are m1_m2:ClC1=NC=C(C=N1)Br, amount is: 0.0 MOLE;m1_m2:S1C=C(C=C1)[Sn](CCCC)(CCCC)CCCC, 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:ClC1=NC=C(C=N1)C1=CSC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Chloro-5-bromopyrimidine and 3-thienyltributyltin are treated in the same manner as in Example 190 to give 2-chloro-5-(3-thienyl)pyrimidine. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=NC=C(C=N1)O, amount is: 0.0 ;m1_m2_m3_m4:ClCC1=CSC=C1, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:CN(C=O)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=NC=C(C=N1)OCC1=CSC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-chloro-5-hydroxypyrimidine (200 mg), 3-chloromethylthiophene (610 mg), potassium carbonate (635 mg) and dimethylformamide (3 ml) is stirred at 50° C. for one hour. After the reaction is complete, to the reaction mixture is added water, and extracted with ethyl acetate. The organic layer is washed with water and saturated brine, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=20:1→20:3), and evaporated to remove the solvent to give 2-chloro-5-(3-thienylmethoxy)pyrimidine (345 mg) as colorless needles. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C1(=CC=CC=C1)[C@H]1NC(OC1)=O, amount is: 0.0 ;m1_m3_m2:[H-].[Na+], amount is: 0.0 ;m1_m3_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m4:[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 .Products are 0:C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)[C@H]1NC(OC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of (R)-4-phenyl-2-oxazolidinone (174 mg, 1.06 mmol) in THF (4 mL) at 0° C., add NaH (4.3 mg, 60% emulsion in oil, 0.106 mmol). Allow the temperature to rise to room temperature over 30 min., then add tetra n-butylammonium bromide (34 mg, 0.106 mmol) to the mixture and stir for another 30 min. to obtain (R)-4-phenyl-2-oxazolidinone tetra n-butylammonium salt. |
Here is a chemical reaction formula: Reactants are m1_m2_m7_m3_m4_m5:C1(=CC=CC=C1)NC1=CC=C(C=C1)NC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m7_m3_m4_m5:IC1=CC=C(C=C1)Cl, amount is: 0.0 ;m1_m2_m7_m3_m4_m5:C1COCCOCCOCCOCCOCCO1, amount is: 0.0 ;m1_m2_m7_m3_m4_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m7_m3_m4_m5:ClC1=C(C=CC=C1)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m8_m6_m0:CCCCCC, amount is: 0.0 MOLE;m8_m6_m0:C(Cl)Cl, amount is: 0.0 MOLE,Catalysts are m1_m2_m7_m3_m4_m5:[Cu], amount is: 0.0 .Products are 0:C1(=CC=CC=C1)N(C1=CC=C(C=C1)N(C1=CC=C(C=C1)Cl)C1=CC=CC=C1)C1=CC=C(C=C1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 1 L, three-necked, round-bottomed flask, equipped with an overhead stirrer, a nitrogen inlet and a reflux condenser, was charged with N,N'-diphenyl-1,4-phenylenediamine (13.0 g, 0.05 mol), 4-iodochlorobenzene (31.0 g, 0.13 mol), copper bronze powder (12.7 g, 0.20 mol), 18-crown-6 ether (2.6 g, 0.10 mol), powdered potassium carbonate (50.1 g. 0.36 mol) and 1,2-dichlorobenzene (120 mL). With a slow purge of nitrogen through the condenser, the reaction vessel was placed in an oil bath and the stirred reaction was heated at 200° C. for 20 hours. The hot reaction mixture was filtered through a bed of filtering aid, which was washed with toluene (50 mL), and the filtrate was concentrated on a rotavapor under reduced pressure. The solvent residue was further removed with a Kugelrohr apparatus to afford a dark brown viscous oil. Flash chromatography on a silica gel column (5×25 cm, 5% CH2Cl2 in hexane as eluent) afforded 9.6 g of grey-white solid. The crude product was further washed with toluene and acetone to provide 6.1 g (25%) of off-white powdered material. The polymer of this example is useful for hole transport materials in light-emitting diode devices. |
Here is a chemical reaction formula: Reactants are m1_m2:C1(=CC=CC=C1)NC(NN)=O, amount is: 0.0 MOLE;m1_m2:C(=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(=O)NNC(=O)NC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Other known methods for the preparation of 4-aryl-1,2,4-triazol-3-ones involve the use of hydrazine as a raw material. In one such method, phenylurea is reacted with hydrazine to give a 4-phenylsemicarbazide. The semicarbazide is then condensed with ethyl formate to give the 4-phenyltriazolone. The overall yield from this method is about 20%. In another method, a 4-phenylsemicarbazide is reacted with formic acid to form the 1-formyl-4-phenylsemicarbazide intermediate, followed by intramolecular condensation to the 4-phenyltriazolone. The yield obtained by this method is about 40%. In yet another method, a substituted aniline is converted to the phenylcarbamate derivative. The phenylcarbamate is treated with hydrazine to give the phenylsemicarbazide derivative, followed by condensation with formamidine acetate to give the 4-phenyltriazolone. Each of these methods requires the use of the toxic compound hydrazine. In addition, the methods suffer from low overall yield. |
Here is a chemical reaction formula: Reactants are m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m3:BrCCC=C(F)F, amount is: 0.0 MOLE;m1_m2_m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m3:SC=1SC2=C(N1)C=CC=C2, amount is: 0.0 ;m4:BrCCC=C(F)F, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6:ClCCl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC(=CCCSC=1SC2=C(N1)C=CC=C2)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To the solution of 4-bromo-1,1-difluorobut-1-ene prepared in Example 6 was added potassium carbonate (10.76 g) and 2-mercaptobenzthiazole (9.18 g). The mixture was stirred at 55° C. for 6 hours and then at room temperature overnight. Gas-liquid chromatography of a sample of the reaction mixture showed that a small amount of 4-bromo-1,1-difluorobut-1-ene remained. More potassium carbonate (1.0 g) was added and the mixture heated for another two and a half hours at 55° C., when all of the bromo compound had been consumed. The mixture was cooled to room temperature and filtered. The residue was washed with acetone and the filtrate and washings combined and evaporated under reduced pressure to give the crude product (16.18 g). This was dissolved in dichloromethane. The solution was filtered and washed with dilute sodium hydroxide (2×25 ml) and with brine (2×25 ml), dried over magnesium sulphate, filtered, the filtrate evaporated to give 2-(4,4-difluorobut-3-enyl)thiobenzthiazole, having a gas chromatographic retention time identical with that of an authentic sample. The yield was 63% based on the quantity of 1,4-dibromo-1,1,2-trifluorobutane used in step (b) of Example 1. 2-(4,4-Difluorobut-3-enyl)thiobenzoxazole was prepared in the same way, but using 2-mercapto benzoxazole instead of 2-mercapto benzthiazole. |
Here is a chemical reaction formula: Reactants are m2:SC=1OC2=C(N1)C=CC=C2, amount is: 0.0 MOLE;m1:BrC(C(CCBr)F)(F)F, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC(=CCCSC=1OC2=C(N1)C=CC=C2)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To the solution of 4-bromo-1,1-difluorobut-1-ene prepared in Example 6 was added potassium carbonate (10.76 g) and 2-mercaptobenzthiazole (9.18 g). The mixture was stirred at 55° C. for 6 hours and then at room temperature overnight. Gas-liquid chromatography of a sample of the reaction mixture showed that a small amount of 4-bromo-1,1-difluorobut-1-ene remained. More potassium carbonate (1.0 g) was added and the mixture heated for another two and a half hours at 55° C., when all of the bromo compound had been consumed. The mixture was cooled to room temperature and filtered. The residue was washed with acetone and the filtrate and washings combined and evaporated under reduced pressure to give the crude product (16.18 g). This was dissolved in dichloromethane. The solution was filtered and washed with dilute sodium hydroxide (2×25 ml) and with brine (2×25 ml), dried over magnesium sulphate, filtered, the filtrate evaporated to give 2-(4,4-difluorobut-3-enyl)thiobenzthiazole, having a gas chromatographic retention time identical with that of an authentic sample. The yield was 63% based on the quantity of 1,4-dibromo-1,1,2-trifluorobutane used in step (b) of Example 1. 2-(4,4-Difluorobut-3-enyl)thiobenzoxazole was prepared in the same way, but using 2-mercapto benzoxazole instead of 2-mercapto benzthiazole. |
Here is a chemical reaction formula: Reactants are m3_m2:Br, amount is: 0.0 MOLE;m1:C(C)OC(=O)NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)CC(=O)C(C)(C)C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)CC(=O)C(C)(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (3RS)-Ethyloxycarbonylamino-1-(tert-butylcarbonylmethyl)-2,3-dihydro-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-one (IV, 250 mg, 0.592 mmol) was taken up in dry DCM (10 ml) at 0° C. and saturated with dry HBr gas. The mixture was stoppered and stirred at r.t. for 64 h. The solvent was evaporated and the product partitioned between 1M HCl and EtOAc. The acid portion was basified and extracted with CHCl3 (×3). The extracts were combined and washed with brine, dried and evaporated to give a brown foam (188 mg, 91%), which was not purified further. |
Here is a chemical reaction formula: Reactants are m2_m6:[H-].[Na+], amount is: 0.0 ;m2_m6:CN(C)C=O, amount is: 0.0 ;m4:IC, amount is: 0.0 ;m1:C(=O)NC=1C=C(C(=O)O)C=CC1, amount is: 0.0 ;m3:IC, amount is: 0.0 ;m5:CN(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(=O)N(C)C1=C(C(=O)O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-Formylamino benzoic acid (2.28 g, 13.8 mmol) was taken up in DMF (25 ml) and added dropwise to a suspension of sodium hydride (1.05 g, 80% disp. in oil) in DMF (15 ml) at 0° C. The mixture was allowed to warm to r.t. over 1 h and then iodomethane (0.95 ml) added. A second portion of iodomethane (0.95 ml) was added after 1 h and the mixture stirred at r.t. overnight. The solvent was removed by evaporation and the product partitioned between ethyl acetate and 1M HCl. The organic layer was washed with brine, then filtered (Whatman® 1 PS phase separator) and evaporated. The residue was chromatographed on silica (eluant 60% ethyl acetate in hexanes) to provide the title compound as a colourless solid (2.30 g, 86%). A portion of the ester (900 mg, 4.66 mmol) was taken up in dioxan/water (2/1, v/v, 30 ml) and treated with LiOH.H2O (378 mg, 9 mmol) at r.t. with stirring overnight. The mixture was acidified with 1M HCl and extracted twice with EtOAc. The combined extracts were washed with brine, filtered (Whatman® 1 PS phase separator) and evaporated. The acid (420 mg, 50%) was used in the next step without further purification. |
Here is a chemical reaction formula: Reactants are m1:COC(C1=CC(=CC=C1)N)=O, amount is: 0.0 ;m2_m3_m4:C(CCC=C)(=O)Cl, amount is: 0.0 MOLE;m2_m3_m4:C(CCC=C)(=O)O, amount is: 0.0 ;m2_m3_m4:S(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:N1=CC=CC=C1, amount is: 0.0 ;m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CCC=C)(=O)NC=1C=C(C(=O)OC)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl(3-amino)benzoate (4.5 g, 29.8 mmol) was taken up in DCM (10 ml) and pyridine (1 ml) at 0° C. 4-Pentenoyl chloride (freshly prepared from 4-pentenoic acid (3.0 g, 29.97 mmol) and thionyl chloride (6.6 ml) at r.t. for 1 h, evaporated and azeotroped with DCM) was added dropwise in DCM (3 ml). The mixture was allowed to warm to r.t. and stirred overnight. The mixture was evaporated and partitioned between EtOAc and 1M HCl. The organic portion was washed with 5% KHCO3 and brine, filtered (Whatman® 1PS, phase separator), and evaporated. The residue was chromatographed (eluant 30% EtOAc in hexanes) to provide a colourless oil (2.20 g, 32%). |
Here is a chemical reaction formula: Reactants are m2:[H-].[Na+], amount is: 0.0 ;m1:BrCCCCC(=O)NC=1C=C(C(=O)OC)C=CC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C1N(CCCC1)C=1C=C(C(=O)OC)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The bromide of Example 36 (1.50 g, 4.88 mmol) was taken up in dry DMF (40 ml) and treated with NaH (160 mg, 80% disp. in oil) at 0° C. The mixture was stirred at r.t. under nitrogen for 10 min, then KI (80 mg) added and the mixture heated at 70° C. for 4 h. The mixture was evaporated and partitioned between EtOAc and 1M HCl. The organic portion was washed with 5% KHCO3 and brine, filtered (Whatman® 1 PS, phase separator) and evaporated. The residue was chromatographed (eluant 2% MeOH in EtOAc) to provide a colourless oil (640 mg, 56%). |
Here is a chemical reaction formula: Reactants are m1_m3:O=C1N(CCCC1)C=1C=C(C(=O)OC)C=CC1, amount is: 0.0 ;m2:B.O1CCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1(CCCCC1)C=1C=C(C(=O)OC)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The compound of Example 37 (640 mg, 2.75 mmol) was dissolved in dry THF (30 ml) and borane-tetrahydrofuran complex (5 ml, 1M solution in THF) was added. The mixture was stirred under nitrogen under reflux for 1 h, then cooled and evaporated. The residue was taken up in MeOH/acetic acid (6/1, v/v, 70 ml) and heated under reflux for 3 h, then evaporated and chromatographed (eluant 10% EtOAc in hexanes) to provide a colourless oil (540 mg, 90%). |
Here is a chemical reaction formula: Reactants are m2:O.[OH-].[Li+], amount is: 0.0 ;m1_m4:N1(CCCCC1)C=1C=C(C(=O)OC)C=CC1, amount is: 0.0 ;m3:C(C)(=O)O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 ;m1_m4:O1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1(CCCCC1)C=1C=C(C(=O)O)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The compound of Example 38 (540 mg, 2.466 mmol) was dissolved in dioxan (12 ml) and water (8 ml). Lithium hydroxide hydrate (300 mg, 7.143 mmol) was added and the mixture stirred at 40° C. for 1 h. The mixture was acidified with acetic acid, evaporated, azeotroped with toluene and chromatographed on silica (eluant 60/40/2, v/v/v, EtOAc/hexanes/AcOH) to provide a colourless solid (450 mg, 90%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(N)(OCC)=O, amount is: 0.0 ;m1_m2_m3_m4:O.C(C=O)(=O)O, amount is: 0.0 ;m1_m2_m3_m4:N1N=NC2=C1C=CC=C2, 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 MOLE,this reaction does not need catalysts,Products are 0:C(C)OC(=O)N(CC(=O)O)N1N=NC2=C1C=CC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Ethyl carbamate (69.0 g, 774.5 mmol), glyoxylic acid hydrate (71.3 g, 774.5 mmol) and benzotriazole (92.0 g, 774.5 mmol) were dissolved in toluene (2.3 1) and the mixture was heated with distillation for 3 h to precipitate the product. The mixture was diluted with toluene (totally 2.3 1) and stirred at 15° C. overnight. The resultant precipitate was collected by filtration, washed with toluene (160 ml) and dried to afford the title compound (196.06 g, 96%): mp. 189°-192° C. |
Here is a chemical reaction formula: Reactants are m1_m3:C(C)OC(=O)NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)CC(=O)C(C)(C)C)=O, amount is: 0.0 ;m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)CC(=O)C(C)(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (3RS)-ethoxycarbonylamino-1-(tert-butylcarbonylmethyl)-2,3-dihydro-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-one (10.0 g, 23.7 mmol) in DCM (40 ml) was added to the above solution below 25° C. and the mixture was stirred for 50 h. The mixture was then poured into 3M HCl (80 ml) below 25° C. and the aqueous portion was washed with DCM (10 ml×2). The combined organic portions were extracted with 3M HCl (20 ml). DCM (50 ml) was added to the combined aqueous portions and the mixture was basified to pH 10 with 25% NaOH below 5° C. The organic portion was washed with brine (50 ml) and evaporated. CH3CN (50 ml) was added and the mixture was filtered to remove the small amount of insoluble material. The filtrate was evaporated to give the rifle compound as a brown foam (7.75 g, 93%), which was not purified further. |
Here is a chemical reaction formula: Reactants are m2:C(C)O.Cl, amount is: 0.0 ;m1:C(C)(C)(C)C(=O)CN1C([C@@H](N=C(C2=C1C=CC=C2)C2=NC=CC=C2)NC(=O)NC2=CC(=CC=C2)N(C)C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.C(C)(C)(C)C(=O)CN1C([C@@H](N=C(C2=C1C=CC=C2)C2=NC=CC=C2)NC(=O)NC2=CC(=CC=C2)N(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-((3R)-1-tert-Butylcarbonylmethyl-2,3-dihydro-2-oxo-5-(2-pyridyl)-1H-1,4-benzodiazepin-3-yl)-N'-(3-dimethylaminophenyl)urea (70 g, 136.6 mmol) was taken up in ethanol (1 l) and 2.26M HCl ethanol (63.5 ml, 143.4 mmol) was added dropwise. The mixture was warmed up to 50° C. to afford a clear solution, which was seeded, cooled to 0° C. and stirred at the same temperature overnight. The resultant precipitate was collected by flirtation to provide the title compound as a white crystalline (62.4 g, 82%): top. 181°-184° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m5_m3_m6:CCN(CC)CC, amount is: 0.0 ;m1_m2_m5_m3_m6:ClC(=O)OCC, amount is: 0.0 ;m1_m2_m5_m3_m6:O(C(C)(C)C)C(=O)N(C)C=1C=C(C(=O)O)C=CC1, amount is: 0.0 ;m4_m7:[N-]=[N+]=[N-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5_m3_m6:CC(=O)C, amount is: 0.0 ;m1_m2_m5_m3_m6:CC(=O)C, amount is: 0.0 ;m4_m7:O, amount is: 0.0 ;m9_m8:O, amount is: 0.0 ;m9_m8:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O(C(C)(C)C)C(=O)N(C)C=1C=C(C=CC1)N=C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Et3N (3.71 g, 36.7 mmol) and a solution of ethyl chloroformate (4.31 g, 39.7 mmol) in acetone (10 ml) were successively added dropwise to a solution of 3-(N-tert-butoxylcarbonyl-N-methylamino)benzoic acid (8.0 g, 31.8 mmol) in acetone (64 ml) below 5° C. After stirring for 30 min, a solution of NaN3 (3.10 g, 47.7 mmol) in water (10 ml) was added to the solution below 5° C. The mixture was stirred at the same temperature for a further 1 h, then poured into toluene (80 ml) and water (160 ml). The organic portion was washed with brine, refluxed for 2 h and evaporated. The residue was distilled (100°-105° C./0.9-1.0 mmHg) to afford the title compound (6.2 g, 78%) as a yellow oil. |
Here is a chemical reaction formula: Reactants are m1_m4:C1(=CC=C(C=C1)S(=O)(=O)Cl)C, amount is: 0.0 ;m2_m5:OCC(O)CO, amount is: 0.0 ;m3:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4:N1=CC=CC=C1, amount is: 0.0 MOLE;m2_m5:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:S(=O)(=O)(C1=CC=C(C)C=C1)OCC(O)COS(=O)(=O)C1=CC=C(C)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Compound 2 was synthesized according to the previous reported method with modifications (Benbouzid et al., 1988). p-Toluenesulfonyl chloride (10.29 g, 54 mmol) dissolved in dry pyridine was added to a stirred solution of anhydrous glycerol (2.48 g, 27 mmol) in dry pyridine (30 ml at 0° C.). The solution was added slowly and left to react for 44 hours in the refrigerator (0°-3° C.). The pink mixture was poured over crushed ice and acidified with concentrated HCl. The organic layer was separated and the aqueous layer was washed with methylene chloride (2×50 ml). The combined organic extracts were washed successively with 2N HCl (2×10 ml) and distilled water (2×10 ml) and dried over anhydrous Na2SO4. The filtrate was evaporated and the residual crude product was purified by column chromatography on silica gel to afford Compound 2 as an oil: 9.72 g (24.3 mmol) yield 90%. 1H NMR [Chemical shift (d), multiplicity, coupling constant (Hz), number of protons, atom]: 7.75 (d; J=8.2 Hz; 4H, Har.); 7.35 (d; J=8.2 Hz; 4H; Har.); 4.1 (bs; 4H; H1,3); 3.35 (bs; 1H; H2); 2.4 (s; 6H; 2CH3). 13C NMR (ppm): 145 (C ar.); 131.7 (C ar.); 129.7 (CH ar.); 127.6 (CH ar.); 69.3 (C1,3); 66.7 (C2); 21.2 (CH3). Satisfactory 1H and 13C NMR data as well as mass spectral data were recorded for this compound. These spectra were consistent with the structures shown in FIG. 1. |
Here is a chemical reaction formula: Reactants are m2:O, amount is: 0.0 MOLE;m1_m4_m3:C(CCC)C=1NC(=C(N1)Cl)CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m3:C(Cl)Cl, amount is: 0.0 ,Catalysts are m1_m4_m3:[O-2].[O-2].[Mn+4], amount is: 0.0 .Products are 0:C(CCC)C=1NC(=C(N1)Cl)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of 2-n-butyl-4-chloro-5-hydroxymethylimidazole (15.00 g, 0.0795 mol) and activated manganese dioxide (40.00 g) in 600 ml of methylene chloride was refluxed for 24 h using a water separator. The mixture was filtered hot through a Celite® pad. The Celite® pad was washed several times with hot methylene chloride. The washings were combined with the filtrate and concentrated in vacuo to give 12.81 g (86%) of the aldehyde as a white solid; mp 97°-98° C. |
Here is a chemical reaction formula: Reactants are m5_m3:C(=O)C=CC(=O)OC, amount is: 0.0 ;m1_m4:[H-].[Na+], amount is: 0.0 ;m1_m4:C(C)O, amount is: 0.0 ;m2:Cl.C(CCCC)(=N)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m3:C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CCC)C=1NC=C(N1)CC(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium hydride (2.82 g, 0,117 mol) was dissolved in 30 ml of absolute ethanol at 0° C. Valeramidine hydrochloride (16.71 g, 0.123 mol) was added to this solution, and after 15 minutes the solution was filtered and the collected solid was washed with 20 ml of ethanol and 50 ml of benzene. The combined filtrates were diluted with 750 ml of benzene, 15 g (0.117 mol) of methyl 3-formylacrylate was added, and the mixture was refluxed for 18.5 h using a trap to remove water. The solvents were removed under vacuum and the residue slurried in ether. Evaporation of the ether solution gave the title compound as an oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:IN1C(CCC1=O)=O, amount is: 0.0 ;m1_m2_m3:C(CCC)C=1NC=C(N1)CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ;m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CCC)C=1NC(=C(N1)I)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-iodosuccinimide (148.75 g, 0.661 mol) was added to a stirred solution of 2-n-butyl-4-hydroxymethylimidazole (100.78 g, 0.652 mol) in 500 ml of absolute ethanol. After 20 minutes the solution was heated to 40°-45° C. for 45 minutes, diluted with 2.5 L of water, and chilled. The crystalline product which formed was collected by filtration, washed with water, and dried to give 1.74.5 g (95%) of crystals; mp 166°-166.5° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(CCC)C=1NC(=C(N1)I)CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:ClCCl, amount is: 0.0 ,Catalysts are m1_m3_m2:[O-2].[O-2].[Mn+4], amount is: 0.0 .Products are 0:C(CCC)C=1NC(=C(N1)I)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of 174.1 g (0.62 mol) of 2-n-butyl-5-hydroxymethyl-4-iodoimidazole and 360 g (4.14 mol) of manganese dioxide in 3 L of dichloromethane was refluxed for 24 hr using a trap to remove water. The hot reaction mixture was filtered through a Celite® pad which was then washed with 4.5 L of boiling methylene chloride. The combined filtrates were concentrated to dryness. The residue was dissolved twice in 150 ml of methanol and each time the solution was concentrated to dryness. The residue was dissolved in 130 ml of methanol and chilled. After crystallization stopped, 700 ml of water was added slowly. The mixture was chilled, and the solid was collected by filtration, washed with water and dried to give 145.2 g (84%) of product; mp 104°-105° C. |
Here is a chemical reaction formula: Reactants are m3:[OH-].[NH4+], amount is: 0.0 ;m1_m2_m4_m5:C1(C=2C(C(N1C(CC(=O)O)C1=CC(=C(C=C1)OC)OC1CCCC1)=O)=CC=CC2)=O, amount is: 0.0 ;m1_m2_m4_m5:C(=O)(N1C=NC=C1)N1C=NC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m5:O1CCCC1, amount is: 0.0 ,Catalysts are m1_m2_m4_m5:CN(C1=CC=NC=C1)C, amount is: 0.0 MOLE.Products are 0:C1(C=2C(C(N1C(CC(=O)N)C1=CC(=C(C=C1)OC)OC1CCCC1)=O)=CC=CC2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3-phthalimido-3-(3-cyclopentyloxy-4-methoxyphenyl)propionic acid (2.05 g, 5.00 mmol), 1,1'-carbonyldiimidazole (0.91 g, 5.5 mmol) and 4-dimethylaminopyridine (trace) in tetrahydrofuran (20 mL) was stirred for 1.5 hours under nitrogen at approximately 25° C. To the solution was added ammonium hydroxide (1.07 mL, 16.0 mmol, 28-30%) and stirring was continued for 1.5 hours. A small amount of solid forms during this time. The mixture was concentrated to half its volume and a white solid precipitated. The mixture was filtered, washed with a small amount of tetrahydrofuran, air dried, and dried in vacuo (60° C.,<1 mm) to afford 1.27 g of the product. The product was further purified by flash column chromatography (silica gel, 5% methanol/methylene chloride) and the resulting white solid was dried in vacuo (60° C., <1 mm) to afford 1 g (49%) of the product: mp 165°-166° C.; 1H NMR (CDCl3) δ 7.85-7.61 (m, 4H), 7.16-7.04 (m, 2H), 6.85-6.75 (m, 1H), 5.80 (dd, J=5.8, 10.4 Hz, 1H), 5.66 (br s, 1H), 5.54 (br s, 1H), 4.82-4.70 (m, 1H), 3.80 (s, 3H), 3.71 (dd, J=10.4, 15 Hz, 1H), 3.06 (dd, J=5.8, 15 Hz, 1H), 2.06-1.51 (m, 8H); 13C NMR (CDCl3) δ 171.8, 168.3, 149.8, 147.7, 133.9, 131.8, 131.3, 123.3, 119.9, 114.6, 111.8, 80.4, 56.0, 51.6, 37.9, 32.7, 24.1; Anal. Calcd for C23 H24N2O5. Theoretical: C, 67.63; H, 5.92; N, 6.86. Found: C, 67.25; H, 5.76; N, 6.68. |
Here is a chemical reaction formula: Reactants are m9_m2:C(CCC)[Li], amount is: 0.0 ;m3_m7:C1(CCCC1)OC=1C=C(C=O)C=CC1OC, amount is: 0.0 ;m5:[Cl-].[NH4+], amount is: 0.0 ;m4:C(C)[Mg]Br, amount is: 0.0 ;m1_m6:C[Si](N[Si](C)(C)C)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m9_m2:CCCCCC, amount is: 0.0 MOLE;m3_m7:O1CCCC1, amount is: 0.0 ;m1_m6:O1CCCC1, amount is: 0.0 ;m8:CC#N, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C1(CCCC1)OC=1C=C(C=CC1OC)C(CC)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To an ice bath cooled stirred solution of 1,1,1,3,3,3-hexamethyldisilazane (2.5M, 4.1 mL, 19.5 mmol) in tetrahydrofuran (5 mL) under nitrogen, was added a hexane solution of butyl lithium (7.2 mL, 18 mmol) via syringe. The ice bath was removed and the solution was stirred for 30 minutes at room temperature. This solution then was added dropwise to an ice bath cooled solution of 3-cyclopentoxy-4-methoxybenzaldehyde (3.3 g, 15 mmol) in tetrahydrofuran (5 mL) and the mixture stirred for 20 minutes. An ethereal solution of ethylmagnesium bromide (3M, 10 mL, 30 mmol) then was added dropwise. The reaction solution was allowed to reach room temperature and then was stirred at room temperature. The reaction progress was monitored by HPLC (Waters Nova-Pak/EC 18 column, 3.9×150 mm, 4 micron, 1 mL/min, 240 nm, 35/65, CH3CN/0.1% H3PO4 (aq)) and after 3 hours no starting material remained. The reaction mixture was slowly poured into a saturated solution of ammonium chloride (100 mL). The resulting mixture was extracted with methylene chloride (3×20 mL) and the combined extracts were dried over magnesium sulfate and concentrated in vacuo to yield 5.6 g of product which was further purified by flash column chromatography (silica gel, 250/10/1, methylene chloride/methanol/ammonium hydroxide) to afford 2.5 g (67%) of the product as an oil: 1H NMR (CDCl3) δ 6.91-6.77 (m, 3H), 4.85-4.74 (m, 1H), 3.83 (s, 3H), 3.74 (t, J=6.8 Hz, 1H), 2.02-1.15 (m, 12H), 0.86 (t, J=7.4 Hz, 3H); 13C NMR (CDCl3) δ 148.8, 147.5, 138.8, 118.4, 113.3, 111.8, 80.3, 57.4, 56.0, 32.7, 32.4, 10.9. |
Here is a chemical reaction formula: Reactants are m3_m7:C1(CCC2=CC=CC=C12)OC=1C=C(C=O)C=CC1OC, amount is: 0.0 ;m4:C(C)[Mg]Br, amount is: 0.0 ;m9_m2:C(CCC)[Li], amount is: 0.0 ;m1_m6:C[Si](N[Si](C)(C)C)(C)C, amount is: 0.0 ;m5:[Cl-].[NH4+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m7:O1CCCC1, amount is: 0.0 ;m9_m2:CCCCCC, amount is: 0.0 MOLE;m1_m6:O1CCCC1, amount is: 0.0 ;m8:CC#N, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C1(CCC2=CC=CC=C12)OC=1C=C(C=CC1OC)C(CC)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To an ice bath cooled stirred solution of 1,1,1,3,3,3-hexamethyldisilazane (2.7 mL, 13 mmol) in tetrahydrofuran (5 mL) under nitrogen, was added a hexane solution of butyl lithium (2.5M, 4.8 mL, 12 mmol) via syringe. The ice bath was removed and the solution was stirred for 25 minutes at room temperature. This solution then was added dropwise to an ice bath cooled solution of 3-indanyloxy-4-methoxybenzaldehyde (2.68 g, 10.0 mmol) in tetrahydrofuran (4 mL) and the mixture was stirred for one hour. An ethereal solution of ethylmagnesium bromide (3M, 6.7 mL, 20 mmol) then was added dropwise via syringe. The reaction mixture was heated at reflux and was monitored by HPLC (Waters Nova-Pak/EC 18 column, 3.9×150 mm, 4 micron, 1 mL/min, 240 nm, 40/60, CH3CN/0.1% H3PO4 (aq)). After 48 hours the reaction had reached completion and was allowed to cool to room temperature. The reaction mixture then was slowly poured into a saturated solution of ammonium chloride (80 mL). The resulting mixture was extracted with methylene chloride (3×15 mL) and the combined extracts were dried over magnesium sulfate and concentrated to afford the product which was further purified by flash column chromatography (silica gel, 250/10/1, methylene chloride/methanol/ammonium hydroxide) to afford 0.27 g (9%) of product as an orange solid. |
Here is a chemical reaction formula: Reactants are m2:C(C)[SiH](CC)CC, amount is: 0.0 ;m1_m5_m3:CC(C=C)(C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6_m4:C(CCC)O, amount is: 0.0 MOLE,Catalysts are m6_m4:[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl, amount is: 0.0 MOLE;m1_m5_m3:[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl, amount is: 0.0 MOLE;m1_m5_m3:C(CCC)O, amount is: 0.0 .Products are 0:CC(CC[Si](CC)(CC)CC)(C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Into a four-necked 500 mL-flask equipped with a stirring apparatus, a thermometer and a dropping funnel, 81.2 g (0.943 mole) of 3-methyl-1-buten-3-ol and 0.2 g of an n-butanol solution containing chloroplatinic acid at a concentration of 2 weight % were charged, and they were heated to 80° C. with stirring. From the dropping funnel, 109.6 g (0.943 mole) of triethylsilane was dropwise added into the four-necked flask. After the completion of the addition, they were heated and stirred for about 20 hours. Meanwhile, the proceeding of reaction was traced by gas chromatography analysis. At the stage when the proceeding of the reaction stopped, an additional mount of the above n-butanol solution containing chloroplatinic acid was added for the proceeding of the reaction. The reaction mixture was distilled under reduced pressure to obtain 154.9 g (0.765 mole) of 1,1-dimethyl-3-(triethylsilyl)propyl alcohol as a fraction at 105° C./14-16 torr. |
Here is a chemical reaction formula: Reactants are m1:BrC1=CC=C(C=C1)OC, amount is: 0.0 ;m3:C(C)N(CC)CC, amount is: 0.0 MOLE;m2:C(C=C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 ;m5:O, amount is: 0.0 MOLE,Catalysts are m4:Cl[Pd]Cl, amount is: 0.0 .Products are 0:COC1=CC=C(C=CC(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: p-bromo anisole (8.4 g), acrylic acid (3.9 g), water (13.5 g), PdCl2 (0.3 mg) and triethyamine (14.3 g, 89.3% pure by titration, the balance being water, recovered by phase separation from a previous run) were charged into an autoclave and heated for 2 hours at 130° C. The work up detailed in Example 1 gave 6.5 g (81%) of >98% pure p-methoxy cinnamic acid. |
Here is a chemical reaction formula: Reactants are m1:BrCCCCC, amount is: 0.0 ;m2:C(CCCC)P(CCCCC)=O, amount is: 0.0 ;m3:P(Cl)(Cl)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:ClP(CCCCC)CCCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the procedure of Example 3, 1-bromopentane (181.2 g) was used as starting material to prepare di-n-pentylphosphine oxide (22.4 g), and this compound was further reacted with phosphorus trichloride to give chloro di-n-pentylphosphine, b.p. 88° C. at a pressure of 0.3 mm of mercury. This compound (10.4 g) was added to a solution of hexamethyldisilazane (4.02 g) in dry toluene (10 cm3) under nitrogen, and the solution was heated at 100° C. for 5 hr. with distillation of chlorotrimethylsilane. The solution was cooled to 25° C. and sulphur (1.6 g) was added causing the temperature to rise to 60° C. The solution was heated to 100° C. for 4 hr. and then allowed to cool. Work up as described in Example 3 gave a crude product (10.6 g) which was also titrated in the presence of zinc and found to have a purity of 55% of theoretical (in this case based on MW 425). Further purification by chromatography on silica gel using hexane with increasing amounts of ethyl acetate (0-30% by volume) as eluent gave N-(di-n-pentylphosphinothioyl)-P,P-di-n-pentylphosphinothioic amide (2.4 g) of 95% purity, m.p. 59°-63.5° C. (MS: m/z 426, 31P NMR in CDCl3, singlet 68.3 ppm downfield of H3PO4). The compound of Formula I in which R1 =R2 =R3 =R4 =n-pentyl was tested by the procedure of Test 1. The results show that the product of this Example is a weak extractant for zinc at pH 1.7 but that it extracts zinc selectively in the presence of iron and has good solubility in ESCAID 100. |
Here is a chemical reaction formula: Reactants are m5:S(O)(O)(=O)=O, amount is: 0.0 ;m1_m2_m6:BrC(C)CCC, amount is: 0.0 ;m1_m2_m6:[Mg], amount is: 0.0 ;m3:CC(CCC)[Mg]Br, amount is: 1.0499999523162842 MOLE;m4_m8:P(=O)(OCCCC)(OCCCC)[O-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:C(C)OCC, amount is: 0.0 ;m1_m2_m6:O1CCCC1, amount is: 0.0 ;m4_m8:C(C)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(CCC)P(C(C)CCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A Grignard solution prepared from 2-bromopentane (227.3 g, 1.5 moles) and magnesium (39.6 g) in tetrahydrofuran (500 cm3) was estimated by a standard procedure and found to contain 1.05 moles of 2-pentyl magnesium bromide. The solution was diluted with diethyl ether (250 cm3) and cooled to 10° C. in an atmosphere of nitrogen. A solution of dibutyl phosphate (67.9 g, 0.35 moles) in diethyl ether (500 cm3) was added with stirring during 1 hr. whilst the temperature was maintained at 10°-15° C. The solution was then boiled under reflux for ten min. to complete the reaction. The solution was cooled to 10° C. and 25% aqueous sulphuric acid (500 cm3) was added with stirring during 1 hr. The organic layer was separated and successively extracted with water (two 300 cm3 amounts). 10% aqueous sodium bicarbonate (300 cm3), and water (two 300 cm3 amounts). It was then dried (magnesium sulphate) and filtered and distilled yielding di-2-pentylphosphine oxide (35.0 g), b.p. 110° C. at a pressure of 0.8 mm of mercury. All of this compound was stirred in nitrogen atmosphere with phosphorus trichloride (50 cm3) at 22° C. After 1 hr. it was found by gas chromatography that about 20% remained unreacted; a second addition of phosphorus trichloride (10 cm3) was made and stirring was continued for a further 2 hr. when reaction had reached about 95% completion. The solution was distilled yielding volatile phosphorus compounds and finally chloro di-2-pentylphosphine (27.5 g), b.p. 72°-74° C. under a pressure of 1.5 mm of mercury. |
Here is a chemical reaction formula: Reactants are m1_m3:P(=S)(Cl)(Cl)Cl, amount is: 0.0 ;m2:CC1=C(C=CC(=C1)C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:P(=S)(OC1=C(C=C(C=C1)C)C)(OC1=C(C=C(C=C1)C)C)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Thiophosphoryl chloride (17.0 g) was dissolved in tuoluene (250 cm3) and triethylamine (21.5 g) was added. The solution was stirred at 20° C. and 2,4-dimethylphenol (24.4 g) was added in portions during 1 hr. The mixture was stirred for 2 hr. and then heated and stirred at 80° C. for a further 2 hr. and then cooled and filtered to remove thriethylamine hydrochloride. The toluene was distilled under reduced pressure leaving bis(2,4-dimethylphenyl) chlorothiophosphate (oil, 30.6 g. 31P NMR in CDCl3, singlet 54.57 ppm downfield of H3 PO4). |
Here is a chemical reaction formula: Reactants are m3:S(O)(O)(=O)=O, amount is: 0.0 MOLE;m2_m4:N, amount is: 0.0 MOLE;m2_m4:O1CCCC1, amount is: 0.0 ;m1:P(=S)(OCC)(OCC)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O(P(OCC)(=S)NP(=O)(OCC)OCC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Diethyl chlorothiophosphate (25.04 g, supplied by Aldrich Chemical Company Ltd.) was added dropwise with stirring to a saturated solution of ammonia in tetrahydrofuran (250 cm3). Stirring was continued for two hr. The mixture was filtered to remove precipitated ammonium chloride and then concentrated by distillation of the solvent under reduced pressure to a yellow oil (diethyl thiophosphoramide, 21.0 g, 31P NMR in CDCl3, singlet, 67.4 ppm downfield of H3PO4). Without further purification, this amide (8.5 g) was redissolved in tetrahydrofuran (250 cm3) and sodium hydride (13.2 g of a 20% suspension in toluene) was added with stirring. When hydrogen ceased to be evolved, diethyl chlorothiophosphate (9.5 g) was added dropwise during 15 min. The mixture was stirred and heated at 65° C. for 2 hr. and then cooled and filtered. The solvent was distilled under reduced pressure leaving a yellow oil which was dissolved in dichloromethane (250 cm3) and stirred with dilute sulphuric acid (1 molar to ensure that the pH of the suspension was less than pH 2). The organic phase was separated, dried with magnesium sulphate, filtered, and concentrated by distillation of solvent under reduced pressure yielding tetraethyl thioimidodiphosphate (11.2 g. 31P NMR in CDCl3, singlet, 56.4 ppm downfield of H3PO4). The purity was determined by titration of a sample dissolved in 50% tetrahydrofuran-water with 0.1M aqueous sodium hydroxide solution for the acidic (NH or SH) proton, which was 50% neutralised at pH 6.1. By this method the purity was found to be 77% of theoretical based on molecular weight 321. The compound of Formula I in which R1 =R2 =R3 =R4 =ethoxy was examined as an extractant for zinc by Tests 1 and 2, with the results listed in Tables 1 and 2, which show that it is a weak extractant for zinc with high selectivity over iron. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(C)C1=C(C=C(C=C1)C)O, amount is: 0.0 MOLE;m1_m2_m3:[H-].[Na+], amount is: 0.0 MOLE;m1_m2_m3:P(=S)(Cl)(Cl)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:P(=S)(OC1=C(C=CC(=C1)C)C(C)C)(OC1=C(C=CC(=C1)C)C(C)C)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-isopropyl-5-methylphenol was reacted with sodium hydride and thiophosphoryl chloride using the procedure of Example 21 to form bis(2-isopropyl-5-methylphenyl) chlorothiophosphate (31PNMR, singlet, 57 ppm). This compound was reacted with diphenylphosphonothioic amide by the General Method C(ii) (THF) yielding the compound of Formula I in which R1 =R2 =phenyl and R3 =R4 =2-isopropyl-5-methylphenoxy. Yield 63%; titration purity, 90%, MW593; 31PNMR, quartet 53 ppm. Test 2 (Table 2) showed that the product is a very strong extractant for zinc; however on long standing it crystallised from ESCAID solution. |
Here is a chemical reaction formula: Reactants are m4:N, amount is: 0.0 ;m1_m2:C(C)(=O)[O-], amount is: 0.0 MOLE;m1_m2:C(C)(=O)OC(C(=O)N1C(CC(C2=CC=CC=C12)C)(C)C)C, amount is: 0.0 ;m3:OS(=O)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7_m6:C(C)(=O)O, amount is: 0.0 ;m7_m6:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=C2C(CC(C2=CC=C1)(C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The acetate compound prepared in B (ii) (55 g, GC purity 91%, 0.172 moles) was added over 45 minutes to 98% H2SO4 (50 ml) at 25°-60° C. (exotherm). After stirring for a further 30 minutes at 60° C., water (50 ml) containing acetic acid (10 ml) was cautiously added dropwise and the mixture heated at 100° C. for 3 hours. Petrol (60/80 b.p., 100 ml) was added and the mixture basified to pH 9 with 35% aqueous ammonia (150 ml). Separation of the organic layer, drying (MgSO4) and solvent flash gave the desired product (22.6 g, GC purity 92%, yield 69%). NMR analysis using chiral solvating agent [(-)-2,2,2-trifluoro-1-(9-anthryl)ethanol] showed a 70/30 mixture of enantiomers in favour of the (-)-isomer. |
Here is a chemical reaction formula: Reactants are m1:O[C@H]1[C@H]([C@H](CC1)CC(=O)O)CCCCC, amount is: 0.0 MOLE;m2:[N+](=[N-])=C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:O[C@H]1[C@H]([C@H](CC1)CC(=O)OC)CCCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: It is to be noted that (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetic acid, used as starting product in this variant of the process of the invention, can also be directly methylated, for example by reacting it with an excess of diazomethane in ether solution, to provide pratically pure methyl (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate, which can then be converted into (+)-cis-Hedione® via oxidation. |
Here is a chemical reaction formula: Reactants are m4:C1(=CC=CC=C1)[C@H](C)N, amount is: 0.0 MOLE;m3:C(C(C(=O)O)O)(C(=O)O)O, amount is: 0.0 MOLE;m6:C(C)O, amount is: 0.0 MOLE;m0_m1_m2_m5: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:O[C@H]1[C@H]([C@H](CC1)CC(=O)[O-])CCCCC;0:C1(=CC=CC=C1)[C@H](C)[NH3+];0:O[C@H]1[C@H]([C@H](CC1)CC(=O)O)CCCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: This acid presented the analytical characters of the racemic acid described under b) and a [α]20D =-12° (c=1.15, ethanol) (purity: 99%; e.r. 99.2:0.8). Proceeding in a manner analogous to that described here-above, but using (-)-(S)-1-penylethylamine (Fluka purum; e.r. 98:2), there was obtained (1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate of (S)-1-phenyl-ethylammonium (m.p. 131°-132°; [α]20D =+4°; c=1.05, ethanol) and (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetic acid having [α]20D =+11° (c=1.10, ethanol) (purity: 99%; e.r. 96.5:3.5). |
Here is a chemical reaction formula: Reactants are m3:C(C)(=O)[O-].[Na+], amount is: 0.0 MOLE;m2:C=1C=C[NH+]=CC1.[O-][Cr](=O)(=O)Cl, amount is: 0.0 MOLE;m1:O[C@H]1[C@H]([C@H](CC1)CC(=O)OC)CCCCC, 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:O=C1[C@H]([C@H](CC1)CC(=O)OC)CCCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: This ester (2.85 g) was then oxidized by means of PCC, in the presence of sodium acetate, in a manner analogous to the method described in Example 1 d), to yield 2.68 g of the desired methyl (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate (colorless oil; purity 98.5%; yield 92.7%). |
Here is a chemical reaction formula: Reactants are m2:C(C)N(CC)CC, amount is: 0.0 ;m1_m4_m5:O=C1C(=C(CC1)CC(=O)O)CCCCC, amount is: 0.0 ;m3:[H][H], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4_m5:C1CCOC1, amount is: 0.0 ;m1_m4_m5:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C1[C@H]([C@H](CC1)CC(=O)OC)CCCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 252 mg (1.20 mmole) 3-oxo-2-pentyl-1 cyclopentene-1-acetic acid, in a mixture of 7 ml of THF and 21 ml of methanol, there were added 2 ml of the catalyst solution obtained in a) (0.025 mmole, 0.021 eq.) and 10.4 μl of triethylamine (0.075 mmole, 3 eq.) under stirring at r.t. This solution, prepared in the glass container of a standard autoclave, was introduced in this autoclave, which was locked, put under a pressure of 45×105Pa of hydrogen and stirred at r.t. The reaction was followed by gas chromatography and was completed in about 4 h. After 1 night, the contents were evaporated under vacuum at r.t., the residue taken in ether, washed with HCl 10.1N and then water, dried over MgSO4 and filtered. The thus obtained (+)-(1R)-3-oxo-2-pentyl-1-cyclopentaneacetic acid was esterified by means of diazomethane to yield methyl (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate, the chromatographic analysis (GC) of which indicated 97% purity, 96:4 cis/trans ratio and 95:5 (+)-(1R)-cis/(-)-(1S)-cis ratio. |
Here is a chemical reaction formula: Reactants are m2:COC(=O)C1=CC2=CC=C(C=C2C=C1)C(=O)OC, amount is: 0.0 MOLE;m1:COC(=O)C1=CC2=CC=C(C=C2C=C1)C(=O)OC, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m3:[Cr].[Co], amount is: 0.0 .Products are 0:C1=C(C=CC2=CC(=CC=C12)C(=O)O)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dimethyl-2,6-naphthalenedicarboxylate was hydrolyzed at elevated temperatures and elevated pressures in the batch-mode in a stirred, 300 ml Hastelloy C autoclave reactor. 37.5 Grams of dimethyl-2,6-naphthalenedicarboxylate were charged to the reactor. No catalyst was used. The 2,6-NDA product was separated from the mother liquor by filtration at room temperature followed by washing with about 150 grams of water. The reaction time, temperature, pressure and analysis of the resulting 2,6-naphthalenedicarboxylic acid are provided in Table 2. During each of the runs reported in Table 2, approximately one-half of the solvent was unintentionally lost. This loss of solvent likely caused the removal of methanol from the reaction mixture thereby shifting the equilibrium towards 2,6-naphthalenedicarboxylic acid. Runs 1, 2 and 3 reported in Table 2 were run consecutively in the same autoclave reactor. |
Here is a chemical reaction formula: Reactants are m1:COC(=O)C1=CC2=CC=C(C=C2C=C1)C(=O)OC, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m2:[Ti], amount is: 0.0 MOLE.Products are 0:C1=C(C=CC2=CC(=CC=C12)C(=O)O)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The hydrolysis of dimethyl-2,6-naphthalenedicarboxylate was conducted in the batch-mode in a 2 liter, stirred, titanium-lined reactor. The reaction time, temperature, pressure and analysis of the resulting 2,6-naphthalenedicarboxylic acid are provided in Table 5. |
Here is a chemical reaction formula: Reactants are m3:[OH-].[Na+], amount is: 0.0 ;m1:[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)Cl, amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE;m2:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m5:[Zn], amount is: 0.0 .Products are 0:NC1=C(C=C(C=C1)C1=CC(=C(C=C1)N)S(=O)(=O)O)S(=O)(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 500 mL flask equipped with mechanical stirrer, condenser, addition funnel, and thermometer was charged with 50.0 g (0.255 mol) of 2-nitrobenzene sulfonyl chloride (Aldrich). Upon dropwise addition of 5M aqueous sodium hydroxide (125 mL, 0.625 mol) the reaction mixture warmed to 80° C. and a dark red/brown solution resulted. The mixture was stirred for 1 hour and the flask allowed to cool to room temperature. Next, 52.5 g of zinc dust (0.803 mol, Mallinckrodt) was added in one portion. The reaction mixture turned green and warmed to 40° C. Sodium hydroxide (50 percent w/w, 113.75 g, 1.42 mol) was then cautiously added dropwise. The temperature of the reaction mixture rose quickly and vigorous reflux ensued. The reaction mixture turned black, then light green, and finally gray. After addition was complete, the reaction mixture was heated to 90° C. and stirred for 30 minutes. The reaction mixture was cooled and filtered through diatomaceous earth. The zinc salts were washed several times with water yielding 850 mL of an orange/brown filtrate. The filtrate was immediately transferred to a 2 L flask equipped with mechanical stirrer, condenser, addition funnel, nitrogen inlet, and thermometer. Concentrated hydrochloric acid (250 mL) was added dropwise. A light yellow precipitate formed, leaving a clear yellow supernatant (pH=7). Further addition of acid caused the solid to dissolve and the solution to turn orange and then brown (pH=4). More acid caused a tan precipitate to form and persist. After HCl addition was complete, the temperature had risen to 45° C. and the pH was 1. The reaction mixture was stirred for an additional hour and then cooled in an ice bath. The precipitate was collected by filtration and dried in a vacuum oven at ambient temperature yielding a cake which weighed 11.69 g. The product was purified by dissolving it in 150 mL of hot water containing 13.5 mL of 5M sodium hydroxide. Concentrated HCl (15 mL) was then slowly added to reprecipitate the product. Vacuum filtration and drying in a vacuum oven at ambient temperature yielded 11.07 g (28.6 percent) of 4,4'-diaminobiphenyl-3,3'-disulfonic acid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:C(=C)N(C=O)CCC(=O)OCC, amount is: 0.0 ;m1_m2_m3_m5:C(CN)N, amount is: 0.0 ;m1_m2_m3_m5:C[O-].[Na+], amount is: 0.0 ;m4:C(CN)N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m5:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(=C)N(C=O)CCC(=O)NCCNC(CCN(C=O)C=C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The apparatus of Example 2 was charged with 17.1 grams (0.1 mole) of ethyl 3-(N-vinylformamido)propionate, 3.0 grams (0.05 mole) of ethylenediamine and 0.12 gram of 25% sodium methoxide in methanol solution. The mixture was stirred at 90° C. for 3 hours, after which the ethanol coproduct was removed by distillation at reduced pressure. The mixture was then allowed to cool to room temperature yielding the crude product as a yellow solid. NMR analysis of the reaction mixture indicated nearly complete conversion of the ethylenediamine. The solid was recrystallized from toluene/acetone to give pale yellow crystals of 1,2-di-[3-(N-vinylformamido)propionamido]ethane. 1H NMR (CDCl3) δ, major rotamer: 2.46 (t, 4H, J=6.2 Hz), 3.30 (bs, 4H), 3.86 (t, 4H, J=7.3 Hz), 4.48 (d, 2H, J=8.7 Hz), 4.70 (d, 2H, J=15.8 Hz), 6.54 (d,d, 2H, J=9.1 Hz, J=15.6 Hz), 6.90 (bs, 2H), 8.25 (d, 2Hz, J=5.6 Hz); minor rotamer: most peaks overlapped with peaks of the major rotamer, except, 6.68 (bs, 2H), 7.13 (d,d, 2H, J=9.3 Hz, J=16.3 Hz), 8.14 (d, 2H, J=5.3 H). Major/minor rotamer ratio: 76:24. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:C(=C)N(C=O)CCC(=O)OCC, amount is: 0.0 ;m1_m2_m3_m5:C(CO)O, amount is: 0.0 ;m1_m2_m3_m5:C[O-].[Na+], amount is: 0.0 ;m4:C(C)O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m5:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(=C)N(C=O)CCC(=O)OCCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The apparatus of Example 2 was charged with 17.1 grams (0.1 mol) of ethyl 3-(N-vinylformamido)propionate, 6.2 grams (0.1 mol) of ethylene glycol, and 0.15 gram of 25% sodium methoxide in methanol solution. The mixture was stirred at 90° C. for 2 hours. No evolution of ethanol was observed during the reaction period. Heating for an additional hour at 135° C. also failed to generate a volatile coproduct which indicated no conversion to the desired product. |
Here is a chemical reaction formula: Reactants are m3_m1_m2:Br.N1C(=NCC1)NCCNC=1NCCN1, amount is: 0.0 ;m3_m1_m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m1_m2:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:N1C(=NCC1)NCCNC=1NCCN1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In 1,400 ml of methanol, 200 g of N,N'-bis-(imidazolin-2-yl)ethylenediamine hydrobromide was dissolved and to the solution, 63 g of 85% potassium hydroxide was then added and stirred for 1 hr at 25° C. After potassium bromide precipitated was filtered out, methanol was removed by distillation to obtain N,N'-bis(imidazolin-2-yl)ethylenediamine as a solid. In 680 ml of ethanol, 34 g (0.1 mol) of 4-(phenylsulfonyl)phenylsulfonylacetic acid was heated to dissolve. To the cooled solution was then added 9.8 g (0.05 mol) of N,N'-bis(imidazolin-2-yl)ethylenediamine in ethanol and the resulting mixture was cooled to 10° C. A crystal precipitated was filtered off, washed and air-dried to obtain 42 g of the intended Compound 3 as crystals. NMR (heavy methanol): δ8.2 (q, 8H), 8.0 (m, 4H), 7.6 (m, 6H), 3.7 (s, 8H), 3.4 (s, 4H). |
Here is a chemical reaction formula: Reactants are m1_m2:ClC1=CC=CC=C1, amount is: 0.0 ;m1_m2:[Cl-].[Al+3].[Cl-].[Cl-], amount is: 0.0 ;m3:C1(=CC=C(C=C1)S(=O)(=O)Cl)C, 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:CC1=CC=C(C=C1)S(=O)(=O)C2=CC=C(C=C2)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 150 ml of chlorobenzene, 100.1 g (0.75 mol) of aluminum chloride was added, and further 143 g (0.75 mol) of p-toluenesulfonyl chloride was added dropwise over 1 hour. After stirred for 3 hours at 55° C., the reaction mixture was poured into 1.5 liter of water, and then the obtained crystal was filtered off and washed with n-hexane to obtain 140 g of the intended 4-methyl-4'-chlorodiphenylsulfone. NMR (heavy chloroform): δ7.9-7.8 (m, 4H), 7.5 (m, 2H), 7.3 (d, 2H), 2.4 (s, 3H). |
Here is a chemical reaction formula: Reactants are m2_m3:C(CS)(=O)O, amount is: 0.0 ;m2_m3:[OH-].[K+], amount is: 0.0 ;m5_m1:CC1=CC=C(C=C1)S(=O)(=O)C2=CC=C(C=C2)Cl, amount is: 0.0 ;m4:CC(C)O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5_m1:CN(C=O)C, amount is: 0.0 ;m6:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)CC(=S)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In 250 ml of N,N-dimethylformamide, 140 g of 4-methyl-4'-chlorodiphenylsulfone was dissolved, and further 77 g of thioglycolic acid and 71 g of 85% potassium hydroxide pellet were added and stirred for 6 hours at 120° C. The reaction mixture was poured into 2-propanol and filtered off to obtain a precipitate. After the precipitate obtained was dissolved in water and then the insoluble matter was filtered off, 150 ml of concentrated chloric acid and 500 g of ice were added therein. The formed white crystal was filtered off and washed with water and further recrystallized with a mixed solvent of n-hexane and ethylacetate to obtain 110 g of the intended 4-(4-methylphenylsulfonyl)phenylthio acetic acid. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:CC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)S(=O)(=O)CC(=O)O, amount is: 0.0 MOLE;m0_m1_m2:C(C)C1=CC=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)CC(=S)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)C1=CC=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)S(=O)(=O)CC(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The intended 4-(4-ethylphenylsulfonyl)phenylsulfonyl acetic acid was prepared in the same manner as in the synthesis of 4-(4-methylphenylsulfonyl)phenylsulfonyl acetic acid of Example 6 except that 104 g of 4-(4-ethylphenylsulfonyl)phenylthio acetic acid was used in place of 100 g of 4-(4-methylphenylsulfonyl)phenylthio acetic acid. The yield was 97.1 g. NMR (heavy methanol): δ8.3-8.1 (m, 4H), 7.9 (d, 2H), 7.4 (d, 2H), 4.4 (s, 2H), 2.7 (q, 2H), 1.2 (t, 3H). |
Here is a chemical reaction formula: Reactants are m1_m3:C(=O)(O)[C@H](O)[C@@H](O)C(=O)O.CN(C)C[C@H]1[C@](CCCC1)(O)C1=CC(=CC=C1)OC, amount is: 0.0 ;m2:[OH-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C)C[C@H]1[C@](CCCC1)(O)C1=CC(=CC=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2050 g (4.95 mole) (1S, 2S)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol L-(+)-tartrate from step 2 were dissolved in 4000 ml water and treated with 900 g crushed ice. 1000 ml of 36-38 % (technical) caustic soda solution were added drop-wise with stirring. The mixture was subsequently extracted with 2500 ml dichloromethane, and was extracted with a further 500 ml dichloromethane after phase separation. The combined organic phases were dried over sodium sulphate. After removing the solvent by distillation, 1280 g (99% theoretical) of (1S, 2S)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol were obtained as a syrup. |
Here is a chemical reaction formula: Reactants are m3:C(C1=CC=CC=C1)=O, amount is: 0.0 MOLE;m4:C(CCCCCCC)=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)=O;0:C(CCCCCCC)=O;0:C(CCCCC)C(C=O)=CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The conversion of the benzaldehyde (bald) amounted to 65.6% and the degree of conversion of octanal to 100%. The selectivities of benzaldehyde and octanal to give α-hexylcinnamaldehyde (α-hex) were 94.9% and 96.2%, respectively, while the selectivity of octanal to give α-hexyldecenal (α-HD) was 1.0%. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C1=CC=CC=C1)=O, amount is: 0.0 ;m1_m2_m3:N1CCCC1, amount is: 0.0 ;m1_m2_m3:C1(=CC=CC=C1)NC1=CC=CC=C1, amount is: 0.0 ;m6:C(C)(=O)O, amount is: 0.0 ;m4:C(CCCCCCC)=O, amount is: 6.6479997634887695 MOLE;m7:[OH-].[Na+], amount is: 0.625 MOLE;m8:C(C)(=O)O, amount is: 0.0 ;m5:C(CCCCCCC)=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)C(C=O)=CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The reaction was carried out in a 2.5 litre double-walled glass reactor provided with a cooler, turbine stirrer (6 blades), thermocouple and a submerged metering tube. A mixture of 1065 grams of benzaldehyde (10.0 mol), 48.8 grams of pyrrolidine (0.679 mol) and 1.8 grams of diphenylamine was heated to 85° C. Over a period of 180 minutes, 878 grams of acidified (0.34 meq/gram) octanal (6.648 mol) were metered in at 85° C. Acidification of the octanal was effected with 16.9 grams of acetic acid (0.281 mol). The reaction was allowed to continue at 85° C. for a further 15 minutes. The reaction mixture was cooled to 65° C. and washed at 50° C., for 15 minutes, with 500.3 grams of 5% strength aqueous NaOH solution (0.625 mol). After neutralization with 78 grams of acetic acid (1.30 mol) for 15 minutes at 50° C., the reaction mixture was separated at 50° C., over a period of 5 to 6 minutes. The organic layer (1869.8 grams) contained 25.5% of benzaldehyde, 2.1% of octanal, 59.8% of α-hexylcinnamaldehyde and 4.6% of α-hexyldecenal. The degrees of conversion of benzaldehyde and octanal were 55.2% and 95.5%, respectively. The selectivity in producing α-hexylcinnamaldehyde was 93.5% with respect to benzaldehyde and 81.4% with respect to octanal. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C1=CC=CC=C1)=O, amount is: 0.0 MOLE;m0_m1_m2:C(CCCCCCC)=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)C(C=O)=CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The method of claim 1 or 2, wherein α-hexylcinnamaldehyde is prepared via aldol condensation of benzaldehyde and n-octanal. |
Here is a chemical reaction formula: Reactants are m2_m3:C(C1=CC=CC=C1)Cl, amount is: 0.0 ;m2_m3:O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)O;0:C(C1=CC=CC=C1)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 126.5 g (1 mol) of benzyl chloride and 180 g (10 mol) of water were rapidly heated to reflux in a flask with baffles and propeller stirrer with vigorous stirring (250 rpm) under nitrogen. After 240 min reaction time, the mixture was rapidly cooled, the organic phase was separated off after addition of toluene, and analyzed by gas chromatography. It was found that 48 g of the benzyl chloride had been converted to give a yield of benzyl alcohol of 37 g and about 3.6 g dibenzyl ether, corresponding to a conversion of 38% and a yield of benzyl alcohol of 91%. The hydrochloric acid formed had a concentration of about 7.4%. |
Here is a chemical reaction formula: Reactants are m3:Cl.N1=CC(=CC=C1)S(=O)(=O)Cl, amount is: 0.0 ;m4:C([O-])([O-])=O.[Na+].[Na+], amount is: 0.0 MOLE;m1_m5:COC=1C(=CC=CC1)N, amount is: 0.0 ;m2:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 ;m1_m5:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=C(C=CC=C1)NS(=O)(=O)C=1C=NC=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: o-Anisidine (377 mg, 3.0 mmol) was dissolved in toluene (10 ml) to which were subsequently added pyridine (0.48 ml, 6.0 mmol) and 3-pyridinesulfonylchloride hydrochloride (642 mg, 3.0 mmol) at room temperature. After 1.5 hours of stirring at 100° C., the resulting reaction solution was mixed with water (20 ml), adjusted to pH 7 to 8 with anhydrous sodium carbonate, extracted with ethyl acetate and then washed with water and saturated brine. After drying on anhydrous sodium carbonate and removing the solvent by evaporation, the resulting orange solid was purified by a silica gel column chromatography (ether:hexane=3:1) to obtain a light orange solid which was subsequently washed with an ether-hexane (1:3) mixture solution to obtain 662 mg (83.5%) of the title compound in the form of colorless prism crystals. |
Here is a chemical reaction formula: Reactants are m3:C1(=CC=C(C=C1)S(=O)(=O)Cl)C, amount is: 0.0 ;m1_m5:COC=1C(=CC=CC1)N, amount is: 0.0 ;m4:O, amount is: 0.0 ;m2:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C1(=CC=CC=C1)C, amount is: 0.0 ,Catalysts are m6:CN(C1=CC=NC=C1)C, amount is: 0.0 MOLE.Products are 0:COC1=C(C=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: o-Anisidine (2.34 ml, 20 mmol) was dissolved in toluene (60 ml) to which were subsequently added, with cooling in an ice bath, pyridine (4.58 ml, 60 mmol), p-toluenesulfonyl chloride (3.89 g, 20 mmol) and a catalytically effective amount of 4-dimethylaminopyridine. After 2.5 hours of stirring at room temperature, the resulting reaction solution was mixed-with water (50 ml), extracted with ethyl acetate and then washed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order. After drying on anhydrous magnesium sulfate and removing the solvent by evaporation, the resulting orange solid was dissolved in ethyl acetate (50 ml), adsorbed to anhydrous magnesium sulfate (20 g), eluted with ether and then subjected to evaporation to remove the solvent. The resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution to obtain 3.44 g (62.0%) of the title compound in the form of colorless prism crystals. |
Here is a chemical reaction formula: Reactants are m2:COC1=CC=C(C=C1)S(=O)(=O)Cl, amount is: 0.0 ;m1:COC=1C(=CC=CC1)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:COC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using o-anisidine (1.0 ml, 8.55 mmol) and 4-methoxybenzenesulfonyl chloride (1.78 g, 8.55 mmol), the procedure of Reference Example 2 was repeated to obtain 2.26 g (90.1%) of the title compound in the form of colorless powder. |
Here is a chemical reaction formula: Reactants are m1:COC=1C(=CC=CC1)N, amount is: 0.0 ;m2:FC1=CC=C(C=C1)S(=O)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using o-anisidine (1.0 ml, 8.55 mmol) and 4-fluorobenzenesulfonyl chloride (1.7 g, 8.55 mmol), the procedure of Reference Example 2 was repeated to obtain 2.24 g (93.1%) of the title compound in the form of colorless prism crystals. |
Here is a chemical reaction formula: Reactants are m2:[N+](=O)([O-])C=1C=C(C=CC1)S(=O)(=O)Cl, amount is: 0.0 ;m1:COC=1C(=CC=CC1)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:COC1=C(C=CC=C1)NS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using o-anisidine (1.0 ml, 8.55 mmol) and 3-nitrobenzenesulfonyl chloride (1.95 g, 8.55 mmol), the procedure of Reference Example 2 was repeated to obtain 2.36 g (89.5%) of the title compound in the form of light yellow needle crystals. |
Here is a chemical reaction formula: Reactants are m1:COC1=CC(=CC=C1)N, amount is: 0.0 ;m2:COC1=CC=C(C=C1)S(=O)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:COC1=CC=C(C=C1)S(=O)(=O)NC1=CC(=CC=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using m-anisidine (0.99 ml, 8.55 mmol) and 4-methoxybenzenesulfonyl chloride (1.78 g, 8.55 mmol), the procedure of Reference Example 2 was repeated to obtain 2.50 g (99.7%) of the title compound in the form of light yellow oil. |
Here is a chemical reaction formula: Reactants are m2:COC1=CC=C(C=C1)S(=O)(=O)Cl, amount is: 0.0 ;m1:NC1=C(C#N)C=CC=C1, 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(#N)C1=C(C=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 2-aminobenzonitrile (1.03 g, 8.55 mmol) and 4-methoxybenzenesulfonyl chloride (1.78 g, 8.55 mmol), the procedure of Reference Example 2 was repeated to obtain 1.57 g (63.7%) of the title compound in the form of colorless solid. |
Here is a chemical reaction formula: Reactants are m1:FC(C1=C(N)C=CC=C1)(F)F, amount is: 0.0 ;m2:COC1=CC=C(C=C1)S(=O)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC(C1=C(C=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)OC)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 2-trifluoromethylaniline (1.39 g, 8.55 mmol) and 4-methoxybenzenesulfonyl chloride (1.78 g, 8.55 mmol), the procedure of Reference Example 2 was repeated to obtain 2.14 g (75.5%) of the title compound in the form of colorless solid. |
Here is a chemical reaction formula: Reactants are m2:ClS(=O)(=O)C1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1:COC=1C(=CC=CC1)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:COC1=C(NS(=O)(=O)C2=CC=C(C(=O)O)C=C2)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using o-anisidine (0.585 ml, 5.0 mmol) and 4-(chlorosulfonyl)benzoic acid (1.15 g, 5.0 mmol), the procedure of Reference Example 2 was repeated to obtain 1.47 g (95.5%) of the title compound in the form of pink powder. |
Here is a chemical reaction formula: Reactants are m1:COC=1C(=CC=CC1)N, amount is: 0.0 ;m2:C(C1=CC(=CC=C1)OC)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:COC=1C=C(C(=O)NC2=C(C=CC=C2)OC)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using o-anisidine (1.0 ml, 8.55 mmol) and m-anisoyl chloride (1.2 ml, 8.55 mmol), the procedure of Reference Example 2 was repeated to obtain 2.2 g (100%) of the title compound in the form of brown oil. |
Here is a chemical reaction formula: Reactants are m1_m5:C(#N)C1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m3_m4:COC=1C(=CC=CC1)N, amount is: 0.0 ;m3_m4:[OH-].[Na+], amount is: 0.0 ;m7_m2:S(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C1=CC=CC=C1, amount is: 0.0 ;m6:C(Cl)Cl, amount is: 0.0 ;m7_m2:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In an atmosphere of dry air, 4-cyanobenzoic acid (1.5 g, 10 mmol) was dissolved in benzene (5 ml), and DMF (0.1 ml) and thionyl chloride (2.2 ml, 30 mmol) were added dropwise to the resulting solution at room temperature, followed by 30 minutes of heating under reflux. After removing the solvent by evaporation, the resulting residue was subjected to azeotropy using benzene (10 ml×2) to obtain a yellow solid which was subsequently dissolved in methylene chloride (10 ml) and mixed with o-anisidine (1.16 ml, 10 mmol) and 20% sodium hydroxide aqueous solution (4 ml) with cooling in an ice bath. After 20 minutes of stirring at the same temperature, the resulting mixture was extracted with methylene chloride and then washed with 1N hydrochloric acid, water and saturated brine in that order. After drying on anhydrous magnesium sulfate, the solvent was removed by evaporation, and the resulting light yellow solid was purified by recrystallization (methylene chloride-ether) to obtain 2.36 g (93.6%) of the title compound in the form of creamy-colored crystals. |
Here is a chemical reaction formula: Reactants are m1:COC=1C(=CC=CC1)N, amount is: 0.0 ;m2:C(=O)(O)C1=CC=NC=C1, 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:COC1=C(NC(=O)C2=CC=NC=C2)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using o-anisidine (2.34 g, 19.0 mmol) and 4-carboxypyridine (2.29 g, 19.0 mmol), the procedure of Reference Example 11 was repeated to obtain 4.22 g (97.2%) of the title compound in the form of colorless powder. |
Here is a chemical reaction formula: Reactants are m2_m3:[OH-].[Na+], amount is: 0.0 ;m2_m3:ClCC1=CC=C(C(=O)Cl)C=C1, amount is: 0.0 ;m1_m4:COC=1C(=CC=CC1)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: o-Anisidine (0.69 ml, 6.0 mmol) was dissolved in methylene chloride (10 ml) and, with cooling in an ice bath, mixed with 20% sodium hydroxide (5 ml) and 4-chloromethylbenzoyl chloride (1.17 g, 6.0 mmol). After 30 minutes of stirring at the same temperature, the reaction mixture was extracted with methylene chloride and then washed with 1N hydrochloric acid, water and saturated brine in that order. After drying on anhydrous magnesium sulfate, the solvent was removed by evaporation, and the resulting light beige solid was purified by recrystallization (ether-hexane) to obtain 1.56 g (94.2%) of the title compound in the form of colorless needle crystals. |
Here is a chemical reaction formula: Reactants are m1:NC1=NC=CC=C1, amount is: 0.0 ;m2:C(C1=CC(=CC=C1)OC)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:COC=1C=C(C(=O)NC2=NC=CC=C2)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 2-aminopyridine (670 mg, 7.12 mmol) and m-anisoyl chloride (1.2 ml, 8.55 mmol), the procedure of Reference Example 13 was repeated to obtain 341 mg (21.0%) of the title compound in the form of light yellow oil. |
Here is a chemical reaction formula: Reactants are m1:COC=1C=C(CN)C=CC1, amount is: 0.0 ;m2:ClCC1=CC=C(C(=O)Cl)C=C1, 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:ClCC1=CC=C(C(=O)NCC2=CC(=CC=C2)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 3-methoxybenzylamine (754 mg, 5.39 mmol) and 4-chloromethylbenzoyl chloride (1.17 g, 6.0 mmol), the procedure of Reference Example 13 was repeated to obtain 1.31 g (83.9%) of the title compound in the form of colorless crystals. |
Here is a chemical reaction formula: Reactants are m2_m3:COC=1C(=CC=CC1)N, amount is: 0.0 ;m2_m3:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m4:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE;m1_m5:Cl.CN(CCCN=C=NCC)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: With cooling in an ice bath, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (630 mg, 3.29 mmol) was added to 15 ml of methylene chloride solution containing o-anisidine (368 mg, 2.99 mmol) and 4-nitrobenzoic acid (500 mg, 2.99 mmol). After 1 hour of stirring at the same temperature, the reaction mixture was roughly adjusted to pH 8 with saturated sodium bicarbonate aqueous solution, extracted with methylene chloride and then washed with water and saturated brine in that order. After drying on anhydrous magnesium sulfate, the solvent was removed by evaporation, and the resulting solid material was purified by silica gel column chromatography (methylene chloride) to obtain 712 mg (87.4%) of the title compound in the form of yellow powder. |
Here is a chemical reaction formula: Reactants are m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1:COC1=CC(=CC=C1)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:[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using m-anisidine (2.50 g, 15.0 mmol) and 4-nitrobenzoic acid (2.03 g, 16.5 mmol), the procedure of Reference Example 16 was repeated to obtain 3.80 g (93.2%) of the title compound in the form of light yellow needle crystals. |
Here is a chemical reaction formula: Reactants are m1:COC1=C(N)C=C(C=C1)OC, amount is: 0.0 ;m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC(=C2)OC)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 2,5-dimethoxyaniline (2.53 g, 16.5 mmol) and 4-nitrobenzoic acid (2.51 g, 15.0 mmol), the procedure of Reference Example 16 was repeated to obtain 3.50 g (77.2%) of the title compound in the form of orange needle crystals. |
Here is a chemical reaction formula: Reactants are m1:COC1=CC(=CC=C1)N, amount is: 0.0 ;m2:[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C=1C=C(C(=O)NC2=CC(=CC=C2)OC)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using m-anisidine (2.03 g, 16.5 mmol) and 3-nitrobenzoic acid (2.51 g, 15.0 mmol), the procedure of Reference Example 16 was repeated to obtain 3.72 g (91.3%) of the title compound in the form of colorless powder. |
Here is a chemical reaction formula: Reactants are m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1:COC1=C(N)C=CC(=C1)OC, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=C(C=C2)OC)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 2,4-dimethoxyaniline (2.53 g, 16.0 mmol) and 4-nitrobenzoic acid (2.50 g, 14.8 mmol), the procedure of Reference Example 16 was repeated to obtain 3.72 g (91.3%) of the title compound in the form of yellow needle crystals. |
Here is a chemical reaction formula: Reactants are m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1:NC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=CC=C2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using aniline (1.50 ml, 16.5 mmol) and 4-nitrobenzoic acid (1.77 g, 10.5 mmol), the procedure of Reference Example 16 was repeated to obtain 2.48 g (97.5%) of the title compound in the form of colorless powder. |
Here is a chemical reaction formula: Reactants are m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1:CSC=1C=C(N)C=CC1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)SC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 3-methylthioaniline (1.40 ml, 11.0 mmol) and 4-nitrobenzoic acid (1.67 g, 10.0 mmol), the procedure of Reference Example 16 was repeated to obtain 2.46 g (85.2%) of the title compound in the form of yellow powder. |
Here is a chemical reaction formula: Reactants are m1:FC(C1=C(N)C=CC=C1)(F)F, amount is: 0.0 ;m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC=C2)C(F)(F)F)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 2-trifluoromethylaniline (1.77 g, 11.0 mmol) and 4-nitrobenzoic acid (1.67 g, 10.0 mmol), the procedure of Reference Example 16 was repeated to obtain 474 mg (15.3%) the title compound in the form of colorless powder. |
Here is a chemical reaction formula: Reactants are m1:FC(C=1C=C(N)C=CC1)(F)F, amount is: 0.0 ;m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)C(F)(F)F)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 3-trifluoromethylaniline (1.77 g, 11.0 mmol) and 4-nitrobenzoic acid (1.67 g, 10.0 mmol), the procedure of Reference Example 16 was repeated to obtain 2.48 g (80.0%) of the title compound in the form of colorless powder. |
Here is a chemical reaction formula: Reactants are m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1:NC=1C=NC=CC1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC=2C=NC=CC2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 3-aminopyridine (1.55 g, 16.5 mmol) and 4-nitrobenzoic acid (2.5 g, 15.0 mmol), the procedure of Reference Example 16 was repeated to obtain 1.81 g (49.6%) of the title compound in the form of colorless powder. |
Here is a chemical reaction formula: Reactants are m2:[N+](=O)([O-])C1=C(C(=O)O)C=CC=C1, amount is: 0.0 ;m1:COC1=CC(=CC=C1)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:[N+](=O)([O-])C1=C(C(=O)NC2=CC(=CC=C2)OC)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using m-anisidine (2.03 g, 16.5 mmol) and 2-nitrobenzoic acid (2.51 g, 15.0 mmol), the procedure of Reference Example 16 was repeated to obtain 3.47 g (84.9%) of the title compound in the form of light yellow needle crystals. |
Here is a chemical reaction formula: Reactants are m1:[N+](=O)([O-])C=1C=C(N)C=CC1, amount is: 0.0 ;m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC=C2)[N+](=O)[O-])C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 3-nitroaniline (2.76 g, 16.5 mmol) and 4-nitrobenzoic acid (2.51 g, 15.0 mmol), the procedure of Reference Example 16 was repeated to obtain 3.58 g (83.2%) of the title compound in the form of light yellow crystals. |
Here is a chemical reaction formula: Reactants are m1:C(C=1C(N)=CC=CC1)(=O)OC, amount is: 0.0 ;m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=C(C=CC=C2)C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using methyl anthranilate (3.02 g, 20.0 mmol) and 4-nitrobenzoic acid (3.67 g, 22.0 mmol), the procedure of Reference Example 16 was repeated to obtain 4.20 g (72.9%) of the title compound in the form of light yellow prism crystals. |