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Here is a chemical reaction formula: Reactants are:m3:C(C=C)O;m2:B(F)(F)F;m1:CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)N)SC1)C(=O)O, Reagents are:m4:C(C)N(CC)CC, and Products are 0:C(C=C)OCC=1CS[C@H]2N(C1C(=O)O)C(C2N)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using the procedure of Step A of Example 8, 27.2 g of 7-amino-cephalosporanic acid, 170 ml of the etherate of boron trifluoride, 136 ml of allyl alcohol and 115 ml of triethylamine were reacted and the 9 g of raw product was purified successively twice with hot hydrochloric acid and ammonium hydroxide to obtain 4.72 g of 3-allyloxymethyl-7-amino-ceph-3-eme-4-carboxylic acid. |
Here is a chemical reaction formula: Reactants are:m2:B(F)(F)F;m1:CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)N)SC1)C(=O)O;m3:C(CC)O, Reagents are:m4:C(C)N(CC)CC, and Products are 0:C(CC)OCC=1CS[C@H]2N(C1C(=O)O)C(C2N)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using the procedure of Step A of Example 8, 27.2 g of 7-amino-cephalosporanic acid, 170 ml of the etherate of of boron trifluoride, 131 ml of propanol and 128 ml of triethylamine were reacted to obtain 17.4 g of raw product which was purified with hot hydrochloric acid and ammonium hydroxide to obtain 7.45 g of 3-propoxymethyl-7-amino-ceph-3-eme-4-carboxylic acid. |
Here is a chemical reaction formula: Reactants are:m3:C(C)(C)O;m2:B(F)(F)F;m1:CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)N)SC1)C(=O)O, Reagents are:m4:C(C)N(CC)CC, and Products are 0:C(C)(C)OCC=1CS[C@H]2N(C1C(=O)O)C(C2N)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using the procedure of Step A of Example 8, 27.2 g of 7-amino-cephalosporanic acid, 170 ml of the etherate of boron trifluoride, 134 ml of isopropanol and 125 ml of triethylamine were reacted to obtain 16.25 g of raw product which was purified by two successive treatments with hot hydrochloric acid and ammonium hydroxide to obtain 5.8 g of 3-isopropoxymethyl-7-amino-ceph-3-eme-4-carboxylic acid. |
Here is a chemical reaction formula: Reactants are:m5:Cl;m4:[OH-].[K+];m1_m2_m3_m6:C(C=C)OCCCCCCCCCCI;m1_m2_m3_m6:COC(=O)C=1C=CC(=CC1)O;m1_m2_m3_m6:C([O-])([O-])=O.[K+].[K+], Reagents are:m1_m2_m3_m6:C(C)O, and Products are 0:C(C=C)OCCCCCCCCCCOC1=CC=C(C(=O)O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 70 mmol (22.7 g) of 10-iododecyl allyl ether, 70 mmol (10.6 g) of methyl p-hydroxybenzoate, and 70 mmol (9.6 g) of potassium carbonate were refluxed in absolute ethanol for 15 hours. After addition of an aqueous potassium hydroxide solution (containing 4.0 g of potassium hydroxide) into the reaction solution, the resulting mixture was further heated at 80° C. for 5 hours. After conclusion of the reaction, the reaction solution was acidified with hydrochloric acid, and the acidified reaction solution was then concentrated under reduced pressure. Water was added to the residue to form a suspension, and the insoluble matter was collected and was then dried, to obtain 18.7 g of 4-(10-allyloxydecyloxy)benzoic acid (Yield: 80%). |
Here is a chemical reaction formula: Reactants are:m4:C(C)(=O)O;m1_m2_m5_m3_m6:C(C)OC(OCC)P(OCC)[O-];m1_m2_m5_m3_m6:C(\C=C\C)#N;m1_m2_m5_m3_m6:[H-].[Na+], Reagents are:m1_m2_m5_m3_m6:C(C)O;m1_m2_m5_m3_m6:C(C)O, and Products are 0:C(#N)CC(C)P(OCC)(=O)C(OCC)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 23.5 g of ethyl (diethoxymethyl)phosphonite and 6.7 g of crotononitrile in 30 ml of dry ethanol is added to a stirred mixture of 1.2 g of sodium hydride (50% dispersion in oil) in 30 ml of ethanol at 0° C. under an atmosphere of nitrogen. The reaction mixture is allowed to warm to room temperature and stirred for 4 hours. 1 ml of glacial acetic acid is added and the mixture concentrated under reduced pressure. The resulting crude product is dissolved in 50 ml of ethyl acetate, washed twice with 25 ml of water, and the organic extract is dried over magnesium sulphate, and then concentrated under reduced pressure. The crude product is distilled under reduced pressure to give ethyl 2-cyano-1methylethyl(diethoxymethyl)phosphinate, b.p. 116° C./0.01 mbar, 31P=+42.2 and +42.0 ppm (CDCl3). |
Here is a chemical reaction formula: Reactants are:m1_m2:NCC(CP(OCC)(=O)C(OCC)OCC)C, Reagents are:m1_m2:Cl, and Products are 0:O.NCC(CP(O)O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 6.0 g of ethyl 3-amino-2-methylpropyl(diethoxymethyl)phosphinate in 30 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 7 hours. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 10 ml of water under reduced pressure. The crude product is dissolved in 50 ml of dry ethanol and 5 ml of propylene oxide is added dropwise. The precipitated solid is collected by filtration and dried to give 3-amino-2-methylpropyl-phosphonous acid monohydrate, m.p. 96°-100° C., 31P=+25.8 ppm (D2O). |
Here is a chemical reaction formula: Reactants are:m4:C(C)(=O)O;m1_m2_m5_m3_m6:C(C)OC(OCC)P(OCC)[O-];m1_m2_m5_m3_m6:C(C(=C)C)#N;m1_m2_m5_m3_m6:[H-].[Na+], Reagents are:m1_m2_m5_m3_m6:C(C)O;m1_m2_m5_m3_m6:C(C)O, and Products are 0:C(C)OP(=O)(C(OCC)OCC)CC(C)C#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 23.5 g of ethyl (diethoxymethyl)phosphonite and 6.7 g of methacrylonitrile in 30 ml of ethanol is added dropwise to a stirred mixture of 1.2 g of sodium hydride (50% dispersion in oil) in 30 ml of ethanol at 0° C. under an atmosphere of nitrogen. The reaction mixture is allowed to warm to room temperature and stirred for 4 hours. 1 ml of glacial acetic acid is added and the mixture is concentrated under reduced pressure. The resulting crude product is dissolved in 50 ml of ethyl acetate, washed twice with 25 ml of water, and the organic extract is dried over magnesium sulphate, and then concentrated under reduced pressure. The crude product is distilled under reduced pressure to give ethyl-2-cyanopropyl(diethoxymethyl)phosphinate, b.p. 116° C./0.01 mbar, 31P=+40.4 and +40.3 ppm (CDCl3). |
Here is a chemical reaction formula: Reactants are:m1_m2:C[Si](C)(C)P(OCC)([O-])C(OCC)OCC;m1_m2:C(=C)C(=O)C;m3:C(Cl)(Cl)Cl, Reagents are:m4:O, and Products are 0:O=C(CCP(OCC)(=O)C(OCC)OCC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 15.0 g of ethyl trimethylsilyl(diethoxymethyl)phosphonite are added dropwise to a stirred solution of 3.9 g of methyl vinyl ketone under an atmosphere of nitrogen at room temperature. The mixture is then heated to 50° C. for a period of 1 hour. The mixture is then allowed to cool to room temperature, 25 ml of chloroform is then added followed by 10 ml water and this mixture is vigorously stirred for a period of 0.5 h. The organic layer is then separated, dried over magnesium sulphate and concentrated under reduced pressure and the crude product distilled under reduced pressure to give ethyl 3-oxobutyl(diethoxymethyl)phosphinate, b.p. 130°-135° C./0.02 mbar, 31P=+45.3 ppm (CDCl3). |
Here is a chemical reaction formula: Reactants are:m4:Cl;m1_m5_m2_m3:O=C(CCP(OCC)(=O)C(OCC)OCC)C;m1_m5_m2_m3:C(C)(=O)[O-].[NH4+];m1_m5_m2_m3:C(#N)[BH3-].[Na+], Reagents are:m1_m5_m2_m3:CO, and Products are 0:NC(CCP(OCC)(=O)C(OCC)OCC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 8.0 g of ethyl 3-oxobutyl(diethoxymethyl)phosphinate in 100 ml of methanol is added 22.8 g of ammonium acetate and 1.3 g of sodium cyanoborohydride. The mixture is stirred under an atmosphere of nitrogen at room temperature for a period of 2.5 h, and then left to stand overnight. The mixture is then acidified to pH 2 with the requisite amount of dilute hydrochloric acid and the methanol is evaporated under reduced pressure. The crude product is dissolved in 25 ml of water, washed twice with 20 ml of diethyl ether and the aqueous phase is then made alkaline to pH 12 with potassium hydroxide. The solution is then saturated with sodium chloride and extracted with 3×25 ml of dichloromethane. The organic phase is dried over magnesium sulphate, filtered and evaporated under reduced pressure and the crude product distilled to give ethyl 3-aminobutyl(diethoxymethyl)phosphinate, b.p. 150° C./0.01 mbar, 31P=+46.1 ppm (CDCl3). |
Here is a chemical reaction formula: Reactants are:m1_m2:NCCC(C1=CC=C(C=C1)Cl)P(OCC)(=O)C(OCC)OCC, Reagents are:m1_m2:Cl, and Products are 0:NCCC(C1=CC=C(C=C1)Cl)P(O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 17.9 g of ethyl 3-amino-1-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate in 200 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 6 hours. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 50 ml of water under reduced pressure. The crude product is then dissolved in 50 ml of water, washed twice with 20 ml of diethyl ether and the aqueous layer is then separated and evaporated under reduced pressure. The crude product is then dissolved in 50 ml of ethanol and 5 ml of propylene oxide is added dropwise. The precipitated solid is collected by filtration and dried to give 3-amino-1-(4-chlorophenyl)propylphosphonous acid, m.p. 210°-220° C., 31P=+29.6 ppm (D2O). |
Here is a chemical reaction formula: Reactants are:m4:C(C)(=O)O;m1_m2_m5_m3_m6:C(C)OC(OCC)P(OCC)[O-];m1_m2_m5_m3_m6:ClC1=CC=C(C=CC#N)C=C1;m1_m2_m5_m3_m6:[H-].[Na+], Reagents are:m1_m2_m5_m3_m6:C(C)O;m1_m2_m5_m3_m6:C(C)O, and Products are 0:ClC1=CC=C(C=C1)C(CC#N)P(OCC)(=O)C(OCC)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 25.8 g of ethyl (diethoxymethyl)phosphonite and 18.0 g of 4-chlorocinnamonitrile in 100 ml of ethanol is added to a stirred mixture of 1.2 g of sodium hydride (50% dispersion in oil) in 30 ml of ethanol at 0° C. under an atmosphere of nitrogen. The reaction mixture is allowed to warm to room temperature and stirred for 4 hours. 1 ml of glacial acetic acid is added and the mixture is concentrated under reduced pressure. The resulting crude product is dissolved in 50 ml of ethyl acetate, washed twice with 25 ml of water and the organic extract is dried over magnesium sulphate, and then concentrated under reduced pressure. The crude product is distilled under reduced pressure to give ethyl 1-(4-chlorophenyl)-2-cyanoethyl(diethoxymethyl)phosphinate, b.p. 180°-200° C./0.02 mbar, 31P=+37.9 and +37.8 ppm (CDCl3). |
Here is a chemical reaction formula: Reactants are:m1_m2:NC(CCP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)Cl, Reagents are:m1_m2:Cl, and Products are 0:NC(CCP(O)O)C1=CC=C(C=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 10.5 g of ethyl 3-amino-3-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate in 100 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 2 hours. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure, and co-evaporated twice with 25 ml of water under reduced pressure. The crude product is then dissolved in 20 ml of water, washed twice with 20 ml of diethyl ether and the aqueous layer is then separated and evaporated under reduced pressure. The crude product is dissolved in 50 ml of ethanol and 5 ml of propylene oxide is added dropwise. The precipitated solid is collected by filtration and dried to give 3-amino-3-(4-chlorophenyl)propylphosphonous acid, m.p. 284°-286° C., 31P=+27.2 ppm (D2O). |
Here is a chemical reaction formula: Reactants are:m1_m2:C[Si](C)(C)P(OCC)([O-])C(OCC)OCC;m1_m2:C(=C)C(=O)C1=CC=C(C=C1)Cl;m3:C(Cl)(Cl)Cl, Reagents are:m4:O, and Products are 0:ClC1=CC=C(C(=O)CCP(OCC)(=O)C(OCC)OCC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 17.7 g of ethyl trimethylsilyl(diethoxymethyl)phosphonite is added dropwise to a stirred solution of 11.7 g of 4-chlorophenyl vinyl ketone under an atmosphere of nitrogen, at room temperature. The reaction mixture is stirred for a period of 1 hour, 25 ml of chloroform is added followed by 10 ml of water and this mixture is vigorously stirred for a period of 0.5 h. The organic layer is then separated, dried over magnesium sulphate and concentrated under reduced pressure to give ethyl 2-4-chlorobenzoyl-ethyl(diethoxymethyl)phosphinate as an oil, 31P=+45.5 ppm (CDCl3). |
Here is a chemical reaction formula: Reactants are:m4:Cl;m1_m5_m2_m3:ClC1=CC=C(C(=O)CCP(OCC)(=O)C(OCC)OCC)C=C1;m1_m5_m2_m3:C(C)(=O)[O-].[NH4+];m1_m5_m2_m3:C(#N)[BH3-].[Na+], Reagents are:m1_m5_m2_m3:CO, and Products are 0:NC(CCP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 25.4 g of ethyl 2-(4-chlorobenzoyl)ethyl(diethoxymethyl)phosphinate in 200 ml of methanol is added 52 g of ammonium acetate and 4.23 g of sodium cyanoborohydride. The mixture is stirred under an atmosphere of nitrogen at room temperature for a period of 3 days. The mixture is then acidified to pH 2 with the requisite amount of dilute hydrochloric acid and the methanol is evaporated under reduced pressure. The crude product is dissolved in 25 ml of water, washed twice with 20 ml of diethyl ether and the aqueous layer is then made alkaline to pH 12 with potassium hydroxide. The solution is then saturated with sodium chloride and extracted with 3×25 ml of dichloromethane. The organic phase is dried over magnesium sulphate and then evaporated under reduced pressure to give ethyl 3-amino-3-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate as a viscous oil, 31P=45.9 ppm (CDCl3). |
Here is a chemical reaction formula: Reactants are:m1_m2:NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)Cl, Reagents are:m1_m2:Cl, and Products are 0:NCC(CP(O)O)C1=CC=C(C=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 5.0 g of ethyl 3-amino-2-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate in 60 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 1 h. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 20 ml of water under reduced pressure. The crude product is dissolved in 20 ml of water, washed twice with 20 ml of diethyl ether and the aqueous layer is then separated and evaporated under reduced pressure. The crude product is dissolved in 50 ml ethanol and 5 ml of propylene oxide is added dropwise. The precipitated solid is collected by filtration and dried to give 3-amino-2-(4-chlorophenyl)propylphosphonous acid (1/3M H2O), m.p. 235°-240° C., 31P=+23.9 ppm (D2O). |
Here is a chemical reaction formula: Reactants are:m1_m2:NCC(CP(OCC)(=O)C(OCC)OCC)C1CCCCC1, Reagents are:m1_m2:Cl, and Products are 0:NCC(CP(O)O)C1CCCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 1.4 g of ethyl 3-amino-2-cyclohexylpropyl(diethoxymethyl)phosphinate in 30 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 1 hour. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 10 ml of water under reduced pressure. The crude product is then dissolved in 20 ml of water washed twice with 20 ml of diethyl ether and the aqueous layer is then separated and evaporated under reduced pressure. The crude product is dissolved in 50 ml of dry ethanol and 5 ml of propylene oxide is added dropwise. The precipitated solid is collected by filtration and dried to give 3-amino-2-cyclohexylpropylphosphonous acid m.p. 235°-240° C., 31P=28.2 ppm (D2O). |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=CC=C1, Reagents are:m1_m2_m4:C(C)(C)(C)O;m1_m2_m4:[Rh];m3:C(C)(C)(C)O, and Products are 0:NCC(CP(OCC)(=O)C(OCC)OCC)C1CCCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 3.45 g of ethyl 3-amino-2-phenylpropyl(diethoxymethyl)phosphinate in 25 ml of tertiary butanol is added to 2.0 g of 5% rhodium in alumina, suspended in 25 ml of tertiary butanol. The resulting mixture is hydrogenated at an atmosphere of 150 bar and temperature of 100° C. for a period of 20 hours. The mixture is then filtered and the filtrate is concentrated under reduced pressure. The crude product is chromatographed on silica gel using ethanol as eluent to give ethyl 3-amino-2-cyclohexylpropyl(diethoxymethyl)phosphinate as a viscous oil, 31P=47.1 and +47.0 ppm (CDCl3). |
Here is a chemical reaction formula: Reactants are:m1_m2:NCC(CP(OCC)(=O)C(OCC)OCC)CC1=CC=CC=C1, Reagents are:m1_m2:Cl, and Products are 0:NCC(CP(O)O)CC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 3.5 g of ethyl 3-amino-2-benzylpropyl(diethoxymethyl)phosphinate in 35 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 3 hours. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 20 ml of water under reduced pressure. The crude product is dissolved in 20 ml of water, washed twice with 20 ml of diethyl ether and the aqueous layer is then separated and evaporated under reduced pressure. The crude product is dissolved in 50 ml ethanol and 5 ml of propylene oxide is added dropwise. The precipitated solid is collected by filtration and dried to give 3-amino-2-benzylpropylphosphonous acid, m.p. 205°-212° C., 31P=+26.1 ppm (D2O). |
Here is a chemical reaction formula: Reactants are:m1_m2:NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)Cl, Reagents are:m1_m2:Cl, and Products are 0:Cl.NCC(CP(O)O)C1=CC=C(C=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 5.0 g of ethyl 3-amino-2-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate in 60 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 1 hour. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure, and co-evaporated three times with 20 ml of water under reduced pressure to give 3-amino-2-(4-chlorophenyl)propylphosphonous acid hydrochloride, as a hygroscopic solid, 31P=+30.1 ppm (D2O). |
Here is a chemical reaction formula: Reactants are:m1_m2:NCC(CP(O)O)C1=CC=C(C=C1)Cl;m1_m2:[OH-].[Na+], Reagents are:, and Products are 0:NCC(CP([O-])=O)C1=CC=C(C=C1)Cl.[Na+], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 0.25 g of 3-amino-2-(4-chlorophenyl)propylphosphonous acid in 10 ml of 0.1M sodium hydroxide solution is stirred at room temperature for a period of 1 hour, and then concentrated under reduced pressure to give sodium 3-amino-2-(4-chlorophenyl)propylphosphinate as a hygroscopic solid, 31 p=+26.0 ppm (D2O). |
Here is a chemical reaction formula: Reactants are:m1_m2:NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=CC=C1, Reagents are:m1_m2:Cl, and Products are 0:NCC(CP(O)O)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 4.0 g of ethyl 3-amino-2-phenylpropyl(diethoxymethyl)phosphinate in 40 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 2 h. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 20 ml of water under reduced pressure. The crude product is dissolved in 20 ml of water, washed twice with 20 ml of diethyl ether and the aqueous layer is then separated and evaporated under reduced pressure. The crude product is dissolved in 50 ml ethanol and 5 ml of propylene oxide is added dropwise. The precipitated solid is collected by filtration and dried to give 3-amino-2-phenylpropylphosphonous acid m.p. 228°-235° C., 31 p=+24.3 ppm (D2O). |
Here is a chemical reaction formula: Reactants are:m1_m2:NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)F, Reagents are:m1_m2:Cl, and Products are 0:NCC(CP(O)O)C1=CC=C(C=C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 4.4 g of ethyl 3-amino-2-(4-fluorophenyl)propyl(diethoxymethyl)phosphinate in 40 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 2 h. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 20 ml of water under reduced pressure. The crude product is dissolved in 20 ml of water, washed twice with 20 ml of diethyl ether and the aqueous layer is then separated and evaporated under reduced pressure. The crude product is dissolved in 50 ml ethanol and 5 ml of propylene oxide is added dropwise. The precipitated solid is collected by filtration and dried to give 3-amino-2-(4-fluorophenyl)propylphosphonous acid (1/3M H2O), m.p. 225°-235° C., 31 p=+24.1 ppm (D2O). |
Here is a chemical reaction formula: Reactants are:m1_m2:NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)C, Reagents are:m1_m2:Cl, and Products are 0:NCC(CP(O)O)C1=CC=C(C=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 3.7 g of ethyl 3-amino-2-(4-methylphenyl)propyl(diethoxymethyl)phosphinate in 40 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 1 h. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 20 ml of water under reduced pressure. The crude product is dissolved in 20 ml of water, washed twice with 20 ml of diethyl ether and the aqueous layer is then separated and evaporated under reduced pressure. The crude product is dissolved in 50 ml ethanol and 5 ml of propylene oxide is added dropwise. The precipitated solid is collected by filtration and dried to give 3-amino-2-(4-methylphenyl)propylphosphonous acid, m.p. 250°-255° C., 31 p=+24.5 ppm (D2O). |
Here is a chemical reaction formula: Reactants are:m1_m2:NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)OC, Reagents are:m1_m2:Cl, and Products are 0:NCC(CP(O)O)C1=CC=C(C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 4.6 g of ethyl 3-amino-2-(4-methoxyphenyl)propyl(diethoxymethyl)phosphinate in 30 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 1 hour. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 20 ml of water under reduced pressure. The crude product is dissolved in 20 ml of water, washed twice with 20 ml of diethyl ether and the aqueous layer is then separated and evaporated under reduced pressure. The crude product is dissolved in 50 ml ethanol and 5 ml of propylene oxide is added dropwise. The precipitated solid is collected by filtration and dried to give 3-amino-2-(4-methoxyphenyl)propylphosphonous acid (1/2M H2O), m.p. 260°-265° C., 31 p=+24.5 ppm (D2O). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m5:C(CC(=O)C)(=O)[O-].[Li+];m1_m4_m2_m5:C(=N)(N)NN.Cl;m3:C(C)O, Reagents are:m1_m4_m2_m5:O;m1_m4_m2_m5:O, and Products are 0:C(N)(=N)NN=C(CC(=O)O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Lithium acetoacetate (0.655 g) in 2 ml water treated with 0.665 g aminoguanidine HCl in 1.33 ml water. The solution was heated to reflux over 30 minutes and then allowed to cool. Ethanol (10 ml) was added and the mixture was stored at -20° C. for 24 hrs., then at 4° C. for 24 hrs. The mixture was allowed to reach room temperature and filtered. The filtrate was concentrated to a paste and triturated with 5 ml ethanol. Filtration and washing with ethanol gave 0.522 g of the hydrazone as a microcrystalline powder, melting point 138.6°-140° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:C(CC1=CC=CC=C1)O;m1_m2_m4:BrCCCCCCBr;m3:[OH-].[Na+], Reagents are:m1_m2_m4:S([O-])(O)(=O)=O.C(CCC)[N+](CCCC)(CCCC)CCCC;m5:O, and Products are 0:BrCCCCCCOCCC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of phenethyl alcohol (20 g), 1,6-dibromohexane (195 g) and tetrabutylammonium bisulphate (3.0 g) in 50% w/v NaOH solution (100 ml) was heated at 65-70° for 4h. The cooled reaction mixture was poured into H2O (400 ml) and extracted with CX (2×300 ml). The dried extracts were evaporated in vacuo to give a yellow liquid which was purified by distillation under reduced pressure to give the title compound as a colourless liquid (26 g) b.p. 110°/0.1 mm. T.l.c. (EA) Rf 0.62. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5:[H-].[Na+];m1_m2_m3_m5:C1(=CC=CC=C1)CCCCO;m1_m2_m3_m5:BrCCCCCCBr;m4:O, Reagents are:m1_m2_m3_m5:C1CCOC1, and Products are 0:BrCCCCCCOCCCCC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: NaH (46% dispersion in oil; 6.5 g) was added portionwise to a solution of 4-phenyl-1-butanol (15.0 g) and 1,6-dibromohexane (48.8 g) in THF (200 ml) under nitrogen. The resulting suspension was refluxed for 27 h and treated with H2O (80 ml). The mixture was extracted with ER (2×200 ml) and the dried extract was evaporated to leave an orange oil. The oil was purified on a column of silica (800 ml) [A] to give a yellow oil which on distillation gave the title compound as a colourless oil (15.0 g) b.p. 90-95/0.1 mmHg. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C1(=CC=CC=C1)CCCO;m1_m2_m3:S(=O)(=O)(O)O.BrCCCCCCBr;m1_m2_m3:[OH-].[Na+], Reagents are:m4:O, and Products are 0:BrCCCCCCOCCCC=1C=CC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3-Phenylpropanol (3.00 g) and 1,6-dibromohexane hydrogen sulphate (0.5 g) and 12.5 M aqueous NaOH (16 ml) for 30 h. The mixture was diluted with H2O (80 ml), extracted with ER (3×100 ml), and the combined organic extracts were washed consecutively with H2O (80 ml) and BR (80 ml). The dried extracts were evaporated and the residual oil purified by [FCS], eluting with CX (one columnful), followed by EA-CX (1:20) to give the title compound (5.35 g) as a colourless oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5:[H-].[Na+];m1_m2_m3_m5:COC1=C(C=CC=C1)CCCCO;m1_m2_m3_m5:BrCCCCCCBr;m4:O, Reagents are:m1_m2_m3_m5:C1CCOC1, and Products are 0:BrCCCCCCOCCCCC1=C(C=CC=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: NaH (46% dispersion in oil; 1.36 g) was added portionwise to a solution of 2-methoxybenzenebutanol (5.0 g) and 1,6-dibromohexane (13.8 g) in THF (50 ml). The suspension was refluxed for 20 h and was treated cautiously with H2O (20 ml). The resulting emulsion was extracted with ER (2×50 ml) and the dried extract was evaporated to leave a yellow oil. The oil was purified on a column of silica (Merck 9385, 600 ml) [A] to give the title compound as a colourless oil (5.6 g). T.l.c. [B] Rf 0.2. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:O1CCCC=C1;m1_m2_m3:ClCCCCO, Reagents are:m1_m2_m3:Cl, and Products are 0:ClCCCCOC1OCCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dihydropyran (15.5 g) was added dropwise to a mixture of 4-chlorobutanol (20 g) and hydrochloric acid (18 M, 1 drop) at RT. The mixture was stirred for 30 min and washed with H2O (100 ml), aqueous NaHCO3 (1 M, 50 ml) and BR (50 ml). The dried liquid was heated under reduced pressure to leave the title compound as a colourless liquid (31.9 g). T.l.c. [L] Rf 0.5. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:COC1=CC=C(C=C1)CCO;m1_m2_m4_m3:BrCCCCCCBr;m1_m2_m4_m3:[OH-].[Na+], Reagents are:m5:O;m1_m2_m4_m3:S([O-])(O)(=O)=O.C(CCC)[N+](CCCC)(CCCC)CCCC, and Products are 0:BrCCCCCCOCCC1=CC=C(C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Methoxybenzeneethanol (5.0 g) and 1,6-dibromohexane (23.7 g) were stirred rapidly at RT with tetra-n-butyl ammonium bisulphate (0.94 g) and 12.5 M aqueous NaOH (30 ml) for 16 h. The mixture was diluted with H2O (125 ml), extracted with ER (3×150 ml) and the combined organic extracts were washed consecutively with H2O (125 ml), BR (125 ml), dried and evaporated to give an oil (24.6 g). The oil was purified by [FCS] eluting with ER-CX (0:100→4:96) to give the title compound as a colourless oil (8.30 g). T.l.c. (CX-ER (40:1)) Rf 0.33. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:FC1=CC=C(C=C1)CCO;m1_m2_m4_m3:BrCCCCCBr;m1_m2_m4_m3:[OH-].[Na+], Reagents are:m1_m2_m4_m3:S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC;m5:O, and Products are 0:BrCCCCCOCCC1=CC=C(C=C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Fluorobenzeneethanol (10.0 g), 1,5-dibromopentane (29 ml), tetra-n-butylammonium hydrogen sulphate (3.2 g, 9 mmol), and aqueous 12.5 M NaOH (109 ml) were stirred vigorously at RT overnight. The mixture was diluted with H2O (400 ml), extracted with ER (3×200 ml), and the combined organic extracts were evaporated. The residual oil was purified by [FCS] eluting with CX-ER (100:0→100:6), to give the title compound as a colourless oil (14.37 g). T.l.c. (ER-CX, 19:1) Rf 0.22. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:COC1=CC=C(C=C1)CCCO;m1_m2_m4_m3:BrCCCCCBr;m1_m2_m4_m3:[OH-].[Na+], Reagents are:m1_m2_m4_m3:S([O-])(O)(=O)=O.C(CCC)[N+](CCCC)(CCCC)CCCC;m5:O, and Products are 0:BrCCCCCOCCCC1=CC=C(C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Methoxybenzenepropanol (7.5 g) and 1,5 dibromopentane (30.5 g) were stirred rapidly at RT with tetra-n-butylammonium bisulphate (1.02 g) and 12.5 M aqueous NaOH (36 ml) for 16 h. The mixture was diluted with H2O (170 ml), extracted with ER (3×20 ml) and the combined organic extracts were washed consecutively with H2O (170 ml) and BR (170 ml), dried and evaporated to give an oil (34.8 g). The oil was purified by [FCS] eluting with ER-CX (0:100→4:96) to give the title compound as a colourless oil (8.83 g). T.l.c. (CX-ER 79:1) Rf 0.1. |
Here is a chemical reaction formula: Reactants are:m3:BrCCOCCCC1=CC=CC=C1;m1_m2_m4:CC(C)(C#C)N;m1_m2_m4:[Li+].[NH2-], Reagents are:m5:N;m1_m2_m4:N, and Products are 0:CC(C#CCCOCCCC1=CC=CC=C1)(N)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,1-Dimethylpropargylamine (8.5 g) was added dropwise to a suspension of lithamide [from lithium (1.7 g)] in liquid ammonia (100 ml) at -33°. The mixture was stirred for 90 min and a solution of [3-(2-bromoethoxy)propyl]benzene (21.5 g) in ER (30 ml) was added dropwise. The suspension was stirred at 4 h and ammonia was allowed to evaporate overnight. The residue was treated with H2O (100 ml) and extracted with ER (3×100 ml). The dried extract was evaporated and the residue was distilled to give the title compound as a colourless oil (3.0 g) b.p. 160-165°/0.2 mmHg. T.l.c. (ER) Rf 0.3. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m5:CNC;m1_m2_m4_m5:BrCC(=O)C=1C=CC(=C(C(=O)OC)C1)OCC1=CC=CC=C1;m3:[BH4-].[Na+], Reagents are:m1_m2_m4_m5:C(C)O;m1_m2_m4_m5:C1CCOC1, and Products are 0:CN(CC(O)C=1C=CC(=C(C(=O)OC)C1)OCC1=CC=CC=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dimethylamine (33% in ethanol, 156 ml) was added to a stirred suspension of methyl 5-(bromoacetyl)-2-(phenylmethoxy)benzoate (105.8 g) in absolute ethanol (1l) and THF (1l). The resulting solution was stirred at RT for 2 h, treated with NaBH4 (25 g) and stirred at RT overnight. The solvent was removed in vacuo and H2O (500 ml) was added to the residue. The mixture was extracted with EA (2×500 ml), the combined extracts were washed with H2O and BR, dried (Na2SO4) and concentrated in vacuo. The product was purified twice by [FCS] eluted with EA-methanol-triethylamine (80:20:1) to give the title compound as a fawn solid (59.8 g) m.p. 79-81°. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:[OH-].[Na+];m1_m2_m3_m4:[Cl-].CC(CCCCCCCCCCC[NH2+]CC1=CC=CC=C1)C;m1_m2_m3_m4:ClC1=C(C=CC=C1)C(C(Cl)(Cl)Cl)C1=C(C=CC=C1)Cl, Reagents are:m1_m2_m3_m4:ClC1=CC=CC=C1, and Products are 0:ClC1=C(C=CC=C1)C(=C(Cl)Cl)C1=C(C=CC=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 201.5 g of 28% strength aqueous sodium hydroxide and 2.0 g of dimethyllaurylbenzylammonium chloride were added to a solution of 250 g of 1,1-bis(chlorophenyl)-2,2,2-trichloroethane in 100 g of monochlorobenzene at 50° C. The mixture was heated at reflux (90° C.) for 20 hours. The organic phase was separated by phase separation and was washed three times with 100 g of water. After distillation of the monochlorobenzene, 219.3 g of 1,1-bis(chlorophenyl)-2,2-dichloroethylene were obtained (y=97.8%) with 0.10% of 1,1-bis(chlorophenyl)-2,2,2-trichloroethane. |
Here is a chemical reaction formula: Reactants are:m3_m6:O.NN;m1_m4_m5_m2:CC1=C(C(=CC=C1)C1=CC=CC=C1)C(=O)O;m1_m4_m5_m2:C(C(=O)Cl)(=O)Cl, Reagents are:m7:O;m3_m6:O1CCCC1;m1_m4_m5_m2:O1CCCC1;m1_m4_m5_m2:CN(C=O)C, and Products are 0:CC1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)NN, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 4,-methylbiphenyl-2-carboxylic acid (6.4 g) in tetrahydrofuran (50 ml) were added N,N-dimethylformamide (two drops) and oxalyl chloride (4.4 g). The mixture was stirred for 16 hours at room temperature. The solvent was evaporated to dryness under reduced pressure to give an oil, which was added dropwise to a solution of hydrazine monohydrate (7.5 g) in tetrahydrofuran (50 ml) with stirring, followed by stirring for further 6 hours. The reaction mixture was diluted with water, which was extracted with ethyl acetate. The extract was washed with water and dried. The solvent was evaporated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel to give crude crystals. Recrystallization from chloroform-isopropyl ether afforded the title compound as colorless needles (4.3 g, 63%), m.p.98°-99° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:O=C1N=C(NO1)C1=C(C=CC=C1)C1=CC=C(C=C1)CN1C(=NC2=C1C(=CC=C2)C(=O)OC)CCC;m1_m2:[OH-].[Na+];m3:Cl, Reagents are:, and Products are 0:O=C1N=C(NO1)C1=C(C=CC=C1)C1=CC=C(C=C1)CN1C(=NC2=C1C(=CC=C2)C(=O)O)CCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of methyl 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]-2-propylbenzimidazole-7-carboxylate (703 mg) in 0.3N-NaOH (12 ml) was stirred at 60° C. for one hour, and then adjusted to pH 3 with 0.1N-HCl. Resulting precipitates were extracted with a mixture of chloroform-ethanol (10:1; 150 ml). The solvent was evaporated under reduced pressure, and the residue was crystallized from methanol to give the title compound as colorless prisms (550 mg, 90%), m.p. 169°-171° C. |
Here is a chemical reaction formula: Reactants are:m2:ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl;m1_m3_m4:NC1=C(SC(=C1N)C)C(=O)OC, Reagents are:m1_m3_m4:CN(C=O)C;m1_m3_m4:ClCCl, and Products are 0:CC=1SC(=C2NC(NC21)=O)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Methyl 3,4-diamino-5-methylthiophene-2-carboxylate (3.0 g) was dissolved in a mixture of N,N-dimethyl formamide (5 ml) and dichloromethane (15 ml). To the solution was added triphosgene (2.4 g) in portions. The mixture was stirred for two days at room temperature, and precipitates were collected by filtration, washed with dichloromethane and dried. Resultant white powder (2.4 g) was suspended in N,N-dimethylformamide (25 ml). To the suspension was added sodium hydride (60% in oil; 0.55 g), and the mixture was stirred for three days at room temperature. The solvent was evaporated under reduced pressure. To the residue was added 2N-HCl. Resulting precipitates were collected by filtration, washed with water, ether and methanol successively, followed by drying to afford the title compound (82 g, 53%) as pale brown powder. |
Here is a chemical reaction formula: Reactants are:m2:C1(=CC=CC=C1)C;m1_m3:IC=1C=C(C(=O)OC)C=CC1, Reagents are:m1_m3:IC1=CC=C(C=C1)C;m4:[Cu], and Products are 0:CC1=CC=C(C=C1)C1=CC(=CC=C1)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of methyl 3-iodobenzoate (26.1 g) in 4-iodotoluene (21.9 g) was added copper powder (31.8 g) gradually at 180°-190° C. The mixture was then stirred for 6 hours at 200°-210° C. The reaction mixture was cooled to room temperature, to which was added toluene. Insoluble materials were filtered off, and the filtrate was concentrated to dryness. The residue was purified by column chromatography on silica gel to afford the title compound as a colorless oil (6.61 g, 29%). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5:C(C)(C)(C)OC(=O)NC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-];m1_m2_m3_m5:BrCC1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)N;m1_m2_m3_m5:C(=O)([O-])[O-].[K+].[K+];m4:O, Reagents are:m1_m2_m3_m5:C(C)#N, and Products are 0:C(C)(C)(C)OC(=O)N(CC1=CC=C(C=C1)C1=C(C=CC=C1)C(N)=O)C1=C(C(=O)OC)C=CC=C1[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (1.8 g), 4'-bromomethylbiphenyl-2-carboxamide (1.8 g) and K2CO3 (0.86 g) in acetonitrile (25 ml) was heated for 6 hours under reflux. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over MgSO4. The solvent was removed in vacuo, and the residue was purified by column chromatography on silica gel to afford a yellow syrup (2.3 g, 90%). |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:C(C)(C)(C)OC(=O)N(CC1=CC=C(C=C1)C1=C(C=CC=C1)C(N)=O)C1=C(C(=O)OC)C=CC=C1[N+](=O)[O-];m1_m3_m2:Cl, Reagents are:m1_m3_m2:CO, and Products are 0:C(N)(=O)C1=C(C=CC=C1)C1=CC=C(C=C1)CNC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of the compound (2.8 g) obtained in Example (54b) in methanol (15 ml) and 1N-HCl (6 ml) was heated for 2 hours under reflux. After removal of the solvent, the residue was made alkaline with an aqueous solution of NaHCO3, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over MgSO4 and concentrated to dryness. The residue was purified by column chromatography on silica gel, and the product was recrystallized from ethyl acetate - hexane to afford yellow needles (1.6 g, 73%). |
Here is a chemical reaction formula: Reactants are:m2_m3:C(C)OC(OCC)(OCC)OCC;m2_m3:C(C)(=O)O;m1_m4:NC=1C(=C(C(=O)OC)C=CC1)NCC1=CC=C(C=C1)C1=C(C=CC=C1)C(NOC(=O)OCC)=N, Reagents are:m1_m4:O1CCOCC1, and Products are 0:C(C)OC1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C(NOC(=O)OCC)=N)C(=CC=C2)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The pale brown syrup (8.58 g) obtained in Example (57a) was dissolved in dioxane (20 ml). To the solution were added tetraethoxymethane (8.64 g) and acetic acid (1.56 g). The mixture was stirred for 2 hours at 100° C. The reaction mixture was concentrated to dryness. The residue was crystallized from ethyl acetate (50 ml). Resulting crystalline precipitates were collected by filtration to obtain the title compound. |
Here is a chemical reaction formula: Reactants are:m2:N12CCCCCC2=NCCC1;m1_m3:C(C)OC1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C(NOC(=O)OCC)=N)C(=CC=C2)C(=O)OC, Reagents are:m1_m3:C(C)(=O)OCC, and Products are 0:C(C)OC1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C=1NOC(N1)=O)C(=CC=C2)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The crude crystals (4.0 g) obtained in Example (57b) was dissolved in ethyl acetate (50 ml). To the solution was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 3.2 g), and the mixture was stirred for 2 hours at 80° C. The reaction mixture was partitioned between ethyl acetate (50 ml) and 1N HCl (20 ml). The organic layer was washed with water, dried and concentrated to dryness. The residue was crystallized from chloroformethyl acetate to afford the title compound as colorless prisms (2.1 g, 45%), which was in agreement with that obtained in Example (1d). |
Here is a chemical reaction formula: Reactants are:m5:Cl;m3_m4:Cl.CN(CCCN=C=NCC)C;m3_m4:C(CCCCC)OC1=CC=C(OCCCCCC(=O)O)C=C1;m1_m2_m6:C1C(=O)COC1=O;m1_m2_m6:C(C)N(CC)CC, Reagents are:m7:CCOCC;m1_m2_m6:CN(C1=CC=NC=C1)C, and Products are 0:OC1=C(C(OC1)=O)C(CCCCCOC1=CC=C(C=C1)Cl)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring solution of 554 mg (5.54 mmol) of tetronic acid in 20 mL of diemthylformamide is added 850 μL (6.09 mmol) of triethylamine and 220 mg (1.765 mmol) of 4-dimethylaminopyridine at 0° C. Next, 1.26 g (6.63 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1.475 g (6.63 mmol) of 6-[4-(hexyloxy)phenoxy]hexanoic acid are added and the reaction mixture is stirred 2 days at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo giving a yellow solid. Pure material is obtained by trituration in ether, filtering to give 774 mg (43%) of 4-hydroxy-3-[6-(4-chlorophenoxy)-1-oxohexyl]-2(5H)-furanone. |
Here is a chemical reaction formula: Reactants are:m5:Cl;m3_m4:Cl.CN(CCCN=C=NCC)C;m3_m4:C(CCCCCCC\C=C/CCCC)(=O)O;m1_m6_m2_m7:C1C(=O)COC1=O;m1_m6_m2_m7:C(C)N(CC)CC, Reagents are:m8:CO.C(C)(=O)OCC;m1_m6_m2_m7:CN(C=O)C;m1_m6_m2_m7:CN(C1=CC=NC=C1)C, and Products are 0:OC1=C(C(OC1)=O)C(CCCCCCC\C=C/CCCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring solution of 111 mg (1.11 mmol) of tetronic acid in 5 mL of dimethylformamide is added 185 μL (1.33 mmol) of triethylamine and 100 mg of 4-dimethylaminopyridine at 0° C. Next, 303 mg (1.33 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 300 mg (1.33 mmol) of myristoleic acid are added and the reaction mixture is stirred 3 days at room temperature. The reaction is acidified with 1.0N HCl and extracted with four 100 mL portions of ethyl acetate. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude compound. Pure material is obtained by flash chromatography with 10% methanol/ethyl acetate as eluant affording 280 mg (82%) of 4-hydroxy-3-((Z)-1-oxo-9-tetradecenyl)-2(5H)-furanone. |
Here is a chemical reaction formula: Reactants are:m3_m4:Cl.CN(CCCN=C=NCC)C;m3_m4:C(CCCCCCC\C=C/CCCCCC)(=O)O;m1_m6_m2_m7:C1C(=O)COC1=O;m1_m6_m2_m7:C(C)N(CC)CC;m5:Cl, Reagents are:m8:CO.C(C)(=O)OCC;m1_m6_m2_m7:CN(C=O)C;m1_m6_m2_m7:CN(C1=CC=NC=C1)C, and Products are 0:OC1=C(C(OC1)=O)C(CCCCCCC\C=C/CCCCCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring solution of 1.07 g (10.72 mmol) of tetronic acid in 30 mL of dimethylformamide is added 1.64 mL (11.97 mmol) of triethylamine and 428 mg of 4-dimethylaminopyridine at 0° C. Next, 2.44 g (12.77 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 3.0 g (11.79 mmol) of palmitoleic acid are added and the reaction is stirred for 3 days at room temperature. The reaction is acidified with 1.0N HCl and extracted with four 100 mL portions of ethyl acetate. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude compound. Pure material was obtained by flash chromatography with 10% methanol/ethyl acetate as eluant affording 1.3 g (36%) of 4-hydroxy-3-((Z)-1-oxo-9-hexadecenyl)-2(5H)-furanone. |
Here is a chemical reaction formula: Reactants are:m3_m4:Cl.CN(CCCN=C=NCC)C;m3_m4:CCCCCCCCC#CCCCCCCCC(=O)O;m1_m6_m2_m7:C1C(=O)COC1=O;m1_m6_m2_m7:C(C)N(CC)CC;m5:Cl, Reagents are:m1_m6_m2_m7:CN(C=O)C;m1_m6_m2_m7:CN(C1=CC=NC=C1)C;m8:CO.C(C)(=O)OCC, and Products are 0:OC1=C(C(OC1)=O)C(CCCCCCCC#CCCCCCCCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring solution of 1.62 g (17.86 mmol) of tetronic acid in 50 mL of dimethylformamide is added 2.5 mL (17.86 mmol) of triethylamine and 652 mg of 4-dimethylaminopyridine at 0° C. Next, 3.71 g (19.35 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 5.0 g (17.86 mmol) of stearolic acid are added and the reaction is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted with three 50 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude compound. Pure material was obtained by flash chromatography with 10% methanol/ethyl acetate as eluant affording 3.3 g (56%) of 4-hydroxy-3-(1-oxo-9-octadecynyl)-2(5H)-furanone. |
Here is a chemical reaction formula: Reactants are:m3:C(CCCCCCCCCCCCCCCCC)(=O)Cl;m4:Cl;m1_m5_m2_m6:C1C(=O)COC1=O;m1_m5_m2_m6:C(C)N(CC)CC, Reagents are:m1_m5_m2_m6:C(Cl)Cl;m1_m5_m2_m6:CN(C1=CC=NC=C1)C;m7:C(C)(=O)OCC, and Products are 0:OC1=C(C(OC1)=O)C(CCCCCCCCCCCCCCCCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring solution of 1.6 g (16 mmol) of tetronic acid in 75 mL of methylene chloride is added 2.5 mL (17.86 mmol) of triethylamine and 640 mg of 4-dimethylaminopyridine at 0° C. Next, 5.0 g (17.6 mmol) of stearoyl chloride is added and the reaction is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted with two 100 mL portions of methylene chloride. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude compound. Pure material was obtained by trituration with ethyl acetate as affording 3.3 g (58%) of 4-hydroxy-3-(1-oxooctadecyl)-2(5H)-furanone. |
Here is a chemical reaction formula: Reactants are:m1_m6_m2_m7:C1C(=O)COC1=O;m1_m6_m2_m7:C(C)N(CC)CC;m3_m4:Cl.CN(CCCN=C=NCC)C;m3_m4:ClC1=CC=C(OCCCCCCCCC(=O)O)C=C1;m5:Cl, Reagents are:m8:CO.C(C)(=O)OCC;m1_m6_m2_m7:CN(C=O)C;m1_m6_m2_m7:CN(C1=CC=NC=C1)C, and Products are 0:ClC1=CC=C(OCCCCCCCCC(=O)C=2C(OCC2O)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring solution of 736 mg (7.36 mmol) of tetronic acid in 30 mL of dimethylformamide is added 1.2 mL (8.09 mmol) of triethylamine and 300 mg of 4-dimethylaminopyridine at 0° C. Next, 1.7 g (8.86 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 2.6 g (8.06 mmol) of 9-(4-chlorophenoxy)nonanoic acid are added and the reaction is stirred overnight at room temperature. The reaction is acidified with 1.0 N HCl and extracted with four 50 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude compound. Pure material is obtained by flash chromatography with 10% methanol/ethyl acetate as eluant affording 800 mg (30%) of 3-[9-(4-chlorophenoxy)-1-oxononyl]4-hydroxy-2(5H)-furanone. |
Here is a chemical reaction formula: Reactants are:m4:O;m1_m2_m5_m3:C(CCCCCCC\C=C/CCCCCCCC)(=O)O;m1_m2_m5_m3:BrCCCCOC1OCCCC1;m1_m2_m5_m3:C([O-])([O-])=O.[Cs+].[Cs+], Reagents are:m1_m2_m5_m3:O1CCCC1, and Products are 0:O1C(CCCC1)OCCCCOC(CCCCCCC\C=C/CCCCCCCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring solution of 2.0 g (7.0 mmol) of oleic acid and 1.6 g (7.0 mmol) of 2-(4-bromobutoxy)tetrahydro-2H-pyran in 20 mL of tetrahydrofuran is added 2.3 g (7.1 mmol) of cesium carbonate and the reaction mixture is stirred overnight at room temperature. The reaction mixture is poured into water and extracted with three 100 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording 2.9 g (100%) of (Z)-9-octadecenoic acid 4-[(tetrahydro-2H-pyran-2-yl)oxy]butyl ester. Next, 500 mg of Dowex 50W 8X resin is added to a stirring solution of 2.9 g (7.0 mmol) of (Z)-9-octadecenoic acid 4-[(tetrahydro-2H-pyran-2-yl)oxy]butyl ester in 100 mL of 1:1 tetrahydrofuran/methanol and the reaction mixture is stirred overnight at room temperature. The reaction mixture is filtered and concentrated in vacuo affording 2.4 g (100%) of alcohol. Next, 11 mL of 2.0M Jones reagent is added at 0° C. to a stirring solution of 2.4 g (7.0 mmol) of alcohol in 75 mL of acetone and the reaction mixture is stirred for 2 hours. The reaction mixture is poured into water and extracted with three 50 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording 2.1 g (81%) of title compound. |
Here is a chemical reaction formula: Reactants are:m3:C(\C=C(/C)\CCC=C(C)C)Br;m2:CC(C)(C)[Si](OCCC/C(=C/O)/O)(C)C;m1_m5:[H-].[Na+];m4:O, Reagents are:m1_m5:O1CCCC1, and Products are 0:CC(C)(C)[Si](OCCCC(COC\C=C(\CCC=C(C)C)/C)O)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring suspension of 140 mg (4.6 mmol) of 80% NaH in 5 mL of tetrahydrofuran is added 1.07 g (4.6 mmol) of (Z)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-pentene-1,2-diol at 0° C. and the reaction mixture is stirred for 1 hour. Next, 1.0 g (4.6 mmol) of geranyl bromide is added and the reaction is stirred overnight at room temperature. The reaction mixture is poured into water and extracted with three 50 mL portions of ethyl acetate. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording 1.7 g (100%) of (E)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[(3,7-dimethyl-2,6-octadienyl)oxy]-2-pentanol. Next, 1.6 g (4.3 mmol) of (E)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[(3,7-dimethyl-2,6-octadienyl)oxy]-2-pentanol and 800 μL (5.73 mmol) of triethylamine in 20 mL of methylene chloride are added at 0° C. to a stirring solution of 13.3 mL of 20% phosgene in toluene and the reaction mixture is stirred for 1 hour. The reaction mixture is concentrated in vacuo and redissolved in 20 mL of tetrahydrofuran. Next, 1.3 g (4.6 mmol) of oleyl amine is added and the reaction mixture is stirred for 2 hours. The reaction mixture is poured into water and extracted with three 50 mL portions of ether. The organic layers are dried over MgSO4 and concentrated in vacuo affording crude product. Pure material is obtained by flash chromatography with 10% ethyl acetate/hexane as eluant affording 1.67 g (67%) of (Z)-9-octadecenylcarbamic acid (E)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[(3,7-dimethyl-2,6-octadienyl)oxy]methyl]butyl ester. Next, 5 mL of 1.0M tetrabutylammonium fluoride in tetrahydrofuran is added to a stirring solution of 1.67 g (2.5 mmol) of (Z)-9-octadecenylcarbamic acid (E)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]- 1-[[(3,7-dimethyl-2,6-octadienyl)oxy]methyl]butyl ester in 5 mL of tetrahydrofuran and the reaction mixture is stirred overnight. The reaction mixture is poured into water and extracted with three 50 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude product. Pure material is obtained by flash chromatography with 10% ethyl acetate/hexane as eluant affording 722 mg (54%) of (Z)-9-octadecenylcarbamic acid (E)-1-[[(3,7-dimethyl-2,6-octadienyl)oxy]methyl]-4-hydroxybutyl ester. Next, 2 mL of 2.0M Jones reagent is added at 0° C. to a solution of 722 mg (1.33 mmol) of (Z)-9-octadecenylcarbamic acid (E)-1-[[(3,7-dimethyl-2,6-octadienyl)oxy]methyl]-4-hydroxybutyl ester in 12 mL of acetone and the reaction is stirred for 3 hours. The reaction is poured into water and extracted with three 50 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude product. Pure material was obtained by flash chromatography with 35% ethyl acetate/hexane as eluant affording 226 mg (30%) of 5-[((E)-3,7-dimethyl-2,6-octadienyl)oxy]-4-[[((Z)-9-octadecenylamino) carbonyl]oxy]pentanoic acid. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2_m6:[F-].C(CCC)[N+](CCCC)(CCCC)CCCC;m1_m5_m2_m6:CC(C)(C)[Si](OC(C/C(=C/COCC(CCC)OC(NCCCCCCCC\C=C/CCCCCCCC)=O)/C)C=C(C)C)(C)C;m3:O;m4:C(C)(=O)OCC.CCCCCC, Reagents are:m1_m5_m2_m6:O1CCCC1;m1_m5_m2_m6:O1CCCC1, and Products are 0:C\C(=C/COCC(CCCO)OC(NCCCCCCCC\C=C/CCCCCCCC)=O)\CCC=C(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring suspension of 140 mg (4.6 mmol) of 80% NaH in 5 mL of tetrahydrofuran is added 1.07 g (4.6 mmol) of (Z)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-pentene-1,2-diol at 0° C. and the reaction mixture is stirred for 1 hour. Next, 1.0 g (4.6 mmol) of geranyl bromide is added and the reaction is stirred overnight at room temperature. The reaction mixture is poured into water and extracted with three 50 mL portions of ethyl acetate. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording 1.7 g (100%) of (E)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[(3,7-dimethyl-2,6-octadienyl)oxy]-2-pentanol. Next, 1.6 g (4.3 mmol) of (E)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[(3,7-dimethyl-2,6-octadienyl)oxy]-2-pentanol and 800 μL (5.73 mmol) of triethylamine in 20 mL of methylene chloride are added at 0° C. to a stirring solution of 13.3 mL of 20% phosgene in toluene and the reaction mixture is stirred for 1 hour. The reaction mixture is concentrated in vacuo and redissolved in 20 mL of tetrahydrofuran. Next, 1.3 g (4.6 mmol) of oleyl amine is added and the reaction mixture is stirred for 2 hours. The reaction mixture is poured into water and extracted with three 50 mL portions of ether. The organic layers are dried over MgSO4 and concentrated in vacuo affording crude product. Pure material is obtained by flash chromatography with 10% ethyl acetate/hexane as eluant affording 1.67 g (67%) of (Z)-9-octadecenylcarbamic acid (E)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[(3,7-dimethyl-2,6-octadienyl)oxy]methyl]butyl ester. Next, 5 mL of 1.0M tetrabutylammonium fluoride in tetrahydrofuran is added to a stirring solution of 1.67 g (2.5 mmol) of (Z)-9-octadecenylcarbamic acid (E)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]- 1-[[(3,7-dimethyl-2,6-octadienyl)oxy]methyl]butyl ester in 5 mL of tetrahydrofuran and the reaction mixture is stirred overnight. The reaction mixture is poured into water and extracted with three 50 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude product. Pure material is obtained by flash chromatography with 10% ethyl acetate/hexane as eluant affording 722 mg (54%) of (Z)-9-octadecenylcarbamic acid (E)-1-[[(3,7-dimethyl-2,6-octadienyl)oxy]methyl]-4-hydroxybutyl ester. Next, 2 mL of 2.0M Jones reagent is added at 0° C. to a solution of 722 mg (1.33 mmol) of (Z)-9-octadecenylcarbamic acid (E)-1-[[(3,7-dimethyl-2,6-octadienyl)oxy]methyl]-4-hydroxybutyl ester in 12 mL of acetone and the reaction is stirred for 3 hours. The reaction is poured into water and extracted with three 50 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude product. Pure material was obtained by flash chromatography with 35% ethyl acetate/hexane as eluant affording 226 mg (30%) of 5-[((E)-3,7-dimethyl-2,6-octadienyl)oxy]-4-[[((Z)-9-octadecenylamino) carbonyl]oxy]pentanoic acid. |
Here is a chemical reaction formula: Reactants are:m4:C(C)(=O)OCC.CCCCCC;m3:O;m1_m2_m5:CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O;m1_m2_m5:C\C(=C/COCC(CCCO)OC(NCCCCCCCC\C=C/CCCCCCCC)=O)\CCC=C(C)C, Reagents are:m1_m2_m5:CC(=O)C, and Products are 0:C\C(=C/COCC(CCC(=O)O)OC(=O)NCCCCCCCC\C=C/CCCCCCCC)\CCC=C(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring suspension of 140 mg (4.6 mmol) of 80% NaH in 5 mL of tetrahydrofuran is added 1.07 g (4.6 mmol) of (Z)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-pentene-1,2-diol at 0° C. and the reaction mixture is stirred for 1 hour. Next, 1.0 g (4.6 mmol) of geranyl bromide is added and the reaction is stirred overnight at room temperature. The reaction mixture is poured into water and extracted with three 50 mL portions of ethyl acetate. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording 1.7 g (100%) of (E)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[(3,7-dimethyl-2,6-octadienyl)oxy]-2-pentanol. Next, 1.6 g (4.3 mmol) of (E)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[(3,7-dimethyl-2,6-octadienyl)oxy]-2-pentanol and 800 μL (5.73 mmol) of triethylamine in 20 mL of methylene chloride are added at 0° C. to a stirring solution of 13.3 mL of 20% phosgene in toluene and the reaction mixture is stirred for 1 hour. The reaction mixture is concentrated in vacuo and redissolved in 20 mL of tetrahydrofuran. Next, 1.3 g (4.6 mmol) of oleyl amine is added and the reaction mixture is stirred for 2 hours. The reaction mixture is poured into water and extracted with three 50 mL portions of ether. The organic layers are dried over MgSO4 and concentrated in vacuo affording crude product. Pure material is obtained by flash chromatography with 10% ethyl acetate/hexane as eluant affording 1.67 g (67%) of (Z)-9-octadecenylcarbamic acid (E)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[(3,7-dimethyl-2,6-octadienyl)oxy]methyl]butyl ester. Next, 5 mL of 1.0M tetrabutylammonium fluoride in tetrahydrofuran is added to a stirring solution of 1.67 g (2.5 mmol) of (Z)-9-octadecenylcarbamic acid (E)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]- 1-[[(3,7-dimethyl-2,6-octadienyl)oxy]methyl]butyl ester in 5 mL of tetrahydrofuran and the reaction mixture is stirred overnight. The reaction mixture is poured into water and extracted with three 50 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude product. Pure material is obtained by flash chromatography with 10% ethyl acetate/hexane as eluant affording 722 mg (54%) of (Z)-9-octadecenylcarbamic acid (E)-1-[[(3,7-dimethyl-2,6-octadienyl)oxy]methyl]-4-hydroxybutyl ester. Next, 2 mL of 2.0M Jones reagent is added at 0° C. to a solution of 722 mg (1.33 mmol) of (Z)-9-octadecenylcarbamic acid (E)-1-[[(3,7-dimethyl-2,6-octadienyl)oxy]methyl]-4-hydroxybutyl ester in 12 mL of acetone and the reaction is stirred for 3 hours. The reaction is poured into water and extracted with three 50 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude product. Pure material was obtained by flash chromatography with 35% ethyl acetate/hexane as eluant affording 226 mg (30%) of 5-[((E)-3,7-dimethyl-2,6-octadienyl)oxy]-4-[[((Z)-9-octadecenylamino) carbonyl]oxy]pentanoic acid. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:COC(CCCCCCCC=CC1=CC=C(C=C1)Cl)=O;m1_m4_m2_m3:O;m1_m4_m2_m3:[OH-].[K+], Reagents are:m1_m4_m2_m3:CO, and Products are 0:ClC1=CC=C(C=C1)C=CCCCCCCCC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1.62 g of 10-(4-chlorophenyl)-dec-9-enoic acid methyl ester in 200 mL of 4:1 methanol:water is added 5.4 g of KOH. The solution is stirred for 2 hours and extracted three times with diethyl ether. The aqueous layer is acidified with concentrated hydrochloric acid, and extracted three times with diethyl ether. The organic layers are combined, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give a yellow oil. The residue is purified via flash chromatography on a 40 mm×150 mm silica column eluting with 40% ethyl acetate/hexane to give 1.6 g (100%) of pure 10-(4-chlorophenyl)dec-9-enoic acid as a mixture of E and Z isomers. |
Here is a chemical reaction formula: Reactants are:m3_m4:Cl.CN(CCCN=C=NCC)C;m3_m4:ClC1=CC=C(C=C1)C=CCCCCCCCC(=O)O;m1_m6_m2_m7:C1C(=O)COC1=O;m1_m6_m2_m7:C(C)N(CC)CC;m5:Cl, Reagents are:m1_m6_m2_m7:CN(C=O)C;m1_m6_m2_m7:CN(C1=CC=NC=C1)C, and Products are 0:OC1=C(C(OC1)=O)C(CCCCCCCC=CC1=CC=C(C=C1)Cl)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring solution of 189 mg (1.89 mmol) of tetronic acid in 15 mL of dimethylformamide is added 290 μL (2.08 mmol) of triethylamine and 8 mg (66 μmol) of 4-dimethylaminopyridine at 0° C. Next, 427 mg (2.22 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 690 mg (2.20 mmol) of 10-(4-chlorophenyl)dec-9-enoic acid as a mixture of E and Z isomers are added and the reaction mixture is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with ethyl acetate. The combined organic layers are washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue is purified via flash chromatography on a 40 mm×150 mm silica gel column eluting with 5% methanol/ethyl acetate to give 400 mg (58%) of pure 4-hydroxy-3-[10-(4-chlorophenyl)-1-oxodec-9-enyl] -2(5H)-furanone as a mixture of E and Z isomers. |
Here is a chemical reaction formula: Reactants are:m2:[H][H];m1_m3_m4:OC1=C(C(OC1)=O)C(CCCCCCCC=CC1=CC=C(C=C1)Cl)=O, Reagents are:m1_m3_m4:C(C)(=O)OCC;m1_m3_m4:[Pd], and Products are 0:OC1=C(C(OC1)=O)C(CCCCCCCCCC1=CC=C(C=C1)Cl)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1.58 g (4.35 mmol) of 4-hydroxy-3-[10-(4-chlorophenyl)-1-oxodec-9-enyl]-2(5H)-furanone in 100 mL of ethyl acetate is added 250 mg of 5% palladium on carbon and subjected to atmospheric hydrogenation using a balloon to deliver the hydrogen. After 1.5 hours, the reaction is worked up by filtering through Solka Flok. The filtrate is washed with copious amounts of ethyl acetate and concentrated in vacuo to give 1.05 g (66%) of pure 4-hydroxy-3-[10-(4-chlorophenyl)1-oxodecyl]-2(5H)-furanone. |
Here is a chemical reaction formula: Reactants are:m2:[Br-].ClC=1C=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC1Cl;m1:OC1=C(C(OC1)=O)C(CCCCCCCCCC1=CC=C(C=C1)Cl)=O, Reagents are:, and Products are 0:OC1=C(C(OC1)=O)C(CCCCCCCCCC1=CC(=C(C=C1)Cl)Cl)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using the procedure of Example 41 for the synthesis of 4-hydroxy-3-[10-(4-chlorophenyl)-1-oxodecyl]-2(5H)-furanone above, but using 3,4-dichlorobenzyltriphenylphosphonium bromide in place of 4-chlorobenzyltriphenylphosphonium chloride, there is obtained the title compound. |
Here is a chemical reaction formula: Reactants are:m3_m4:Cl.CN(CCCN=C=NCC)C;m3_m4:C(CCCCCCC\C=C/CCCCCCCC)(=O)O;m1_m6_m2:C1C(=O)CSC1=O;m1_m6_m2:C(C)N(CC)CC;m5:Cl, Reagents are:m1_m6_m2:CN(C=O)C, and Products are 0:OC1=C(C(SC1)=O)C(CCCCCCC\C=C/CCCCCCCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring solution of 1.71 g (14.75 mmol) of thiotetronic acid in 10 mL of dimethylformamide is added 2.22 mL (17.2 mmol) of triethylamine and 592 mg (4.85 mmol) of 4-diemthylaminopyridine at 0° C. Next, 3.38 g (17.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 5.0 g (17.7 mmol) of oleic acid are added and the reaction mixture is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with diethyl ether. The combined organic layers are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is subjected to HPLC chromatography (2 inch Dynamax silica gel column, 25 mL/min) eluting with 100% ethyl acetate to give 1.85 g (33%) of 4-hydroxy-3-[(Z)-1-oxo-9-octadecenyl]-2(5H)-thiophenone as an oil. |
Here is a chemical reaction formula: Reactants are:m5:Cl;m3_m4:Cl.CN(CCCN=C=NCC)C;m3_m4:C(CCCCCCC\C=C/CCCC)(=O)O;m1_m6_m2_m7:C1C(=O)CSC1=O;m1_m6_m2_m7:C(C)N(CC)CC, Reagents are:m1_m6_m2_m7:CN(C=O)C;m1_m6_m2_m7:CN(C1=CC=NC=C1)C, and Products are 0:OC1=C(C(SC1)=O)C(CCCCCCC\C=C/CCCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring solution of 855 mg (7.37 mmol) of thiotetronic acid in 10 mL of dimethylformamide is added 902 μL (6.47 mmol) of triethylamine and 240 mg (1.96 mmol) of 4-dimethylaminopyridine at 0° C. Next, 1.68 g (8.76 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 2.0 g (8.84 mmol) of myristoleic acid are added and the reaction mixture is stirred overnight at room temperature. The reaction is acidified with 1.0 N HCl and extracted three times with diethyl ether. The combined organic layers are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is subjected to HPLC chromatography (2 inch Dynamax silica gel column, 25 mL/min) eluting with 100% ethyl acetate to give 785 mg (33%) of 4-hydroxy-3-[(Z)-1-oxo-9-tetradecenyl]-2(5H)-thiophenone as an oil. |
Here is a chemical reaction formula: Reactants are:m5:Cl;m1_m6_m2_m7:C1C(=O)CSC1=O;m1_m6_m2_m7:C(C)N(CC)CC;m3_m4:Cl.CN(CCCN=C=NCC)C;m3_m4:C(CCCC\C=C/C\C=C/C\C=C/CCCCC)(=O)O, Reagents are:m1_m6_m2_m7:CN(C=O)C;m1_m6_m2_m7:CN(C1=CC=NC=C1)C, and Products are 0:OC1=C(C(SC1)=O)C(CCCC\C=C/C\C=C/C\C=C/CCCCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring solution of 695 mg (6.04 mmol) of thiotetronic acid in 10 mL of dimethylformamide is added 902 μL (6.47 mmol) of triethylamine and 240 mg (1.97 mmol) of 4-dimethylaminopyridine at 0° C. Next, 1.37 g (7.13 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 2.0 g (7.19 mmol) of γ-linolenic acid are added and the reaction mixture is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with diethyl ether. The combined organic layers are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was subjected to HPLC chromatography (2 inch Dynamax silica gel column, 25 mL/min) eluting with 100% ethyl acetate to give 1.8 g (79%) of 4-hydroxy-3-[(Z,Z,Z)-1-oxo-6,9,12-octadecatrienyl]-2(5H)-thiophenone as an oil. |
Here is a chemical reaction formula: Reactants are:m3_m4:Cl.CN(CCCN=C=NCC)C;m3_m4:C(CCCC\C=C/CCCCCCCCCCC)(=O)O;m5:Cl;m1_m6_m2_m7:C1C(=O)CSC1=O;m1_m6_m2_m7:C(C)N(CC)CC, Reagents are:m1_m6_m2_m7:CN(C=O)C;m1_m6_m2_m7:CN(C1=CC=NC=C1)C, and Products are 0:OC1=C(C(SC1)=O)C(CCCC\C=C/CCCCCCCCCCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring solution of 1.71 g (14.7 mmol) of thiotetronic acid in 20 mL of dimethylformamide is added 2.22 mL (15.9 mmol) of triethylamine and 592 mg (4.85 mmol) of 4-dimethylaminopyridine at 0° C. Next, 3.38 g (17.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 5.0 g (17.7 mmol) of petroselinic acid are added and the reaction mixture is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with diethyl ether. The combined organic layers are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is subjected to HPLC chromatography (2 inch Dynamax silica gel column, 25 mL/min) eluting with 100% ethyl acetate to give 1.2 g (21%) of 4-hydroxy-3-[(Z)-1-oxo-6-octadecenyl]-2(5H)-thiophenone as an oil. |
Here is a chemical reaction formula: Reactants are:m4:[OH-].[K+];m3:Cl;m6_m5_m1_m2:C(CCCCCCC\C=C/CCCCCCCC)(=O)OC;m6_m5_m1_m2:ICI, Reagents are:m7:O1CCCC1.CO.O;m6_m5_m1_m2:CCOCC;m6_m5_m1_m2:[Cu].[Zn], and Products are 0:C(CCCCCCC)[C@@H]1[C@@H](C1)CCCCCCCC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 2.2 g of zinc-copper couple in 30 mL of dry ether is added 5.7 mL (16.9 mmol) of methyl oleate and 5.4 mL (70.7 mmol) of diiodomethane. The reaction mixture is refluxed overnight, cooled to room temperature, poured into 1.0N HCl, and extracted three times with ether. The organic layers are combined, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give an oil. The oil is subjected to the conditions described in Example 51 above to give an oil free of starting material. The oil is taken up in a combination of tetrahydrofuran:methanol:water (2:1:1), followed by the addition of 4.0 g of 85% KOH. After 4 hours stirring at room temperature, the solvents are evaporated, the residue taken up in 0.1N KOH, and extracted three times with ether. The aqueous phase is acidified using concentrated HCl and extracted three times with ether. The ether layers are combined, washed with brine, dried over, MgSO4, filtered, and concentrated in vacuo to give cis-8-(2 -octylcyclopropyl) octanoic acid. Spectral data follows: 1H NMR (CDCl3, 400 MHz) δ 2.35 (t, 2H, J=7.0 Hz, CH2C=O), 0.6-1.7 (m, 33H). |
Here is a chemical reaction formula: Reactants are:m2_m5:[Br-].[Na+];m1:C(=C/CCCCCCC)/O;m3_m6:C([O-])(O)=O.[Na+], Reagents are:m4:ClCCl;m2_m5:O;m3_m6:[O-]Cl.[Na+], and Products are 0:C(CCCC)[C@@H]1[C@@H](C1)CC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Cis-nonen-1-ol (10.0 g) is subjected to the cyclopropanation conditions as described in the preparation of Example 52. The resulting residue is taken up in 100 mL of dichloromethane at 0° C., followed by the addition of 800 mg of sodium bromide in 2 mL of water and 150 mg of 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical. To this mixture is added 1.50 g of Aliquot 336 followed by the dropwise addition of 9.2 g of sodium bicarbonate in 230 mL of 5% NaOCl. The aqueous phase is made basic, separated from the organic phase and acidified with concentrated HCl, and then extracted three times with dichloromethane. The combined organic layers are washed with water, dried over MgSO4, and concentrated in vacuo to give cis-2-(2'-pentylcyclopropyl)acetic acid. |
Here is a chemical reaction formula: Reactants are:m3_m6:C([O-])(O)=O.[Na+];m1:C(=C/CCCCCCC)/O;m2_m5:[Br-].[Na+], Reagents are:m3_m6:[O-]Cl.[Na+];m2_m5:O;m4:ClCCl, and Products are 0:C(CCCC)[C@@H]1[C@@H](C1)CC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Cis-nonen-1-ol (10.0 g) is subjected to the cyclopropanation conditions described in the preparation of Example 52. The resulting residue is taken up in 100 mL of dichloromethane at 0° C., followed by the addition of 800 mg of sodium bromide in 2 mL of water and 150 mg of 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical. To this mixture is added 1.50 g of Aliquot 336 followed by the dropwise addition of 9.2 g of sodium bicarbonate in 230 mL of 5% NaOCl. The aqueous phase is made basic, separated from the organic phase and acidified with concentrated HCl, and then extracted three times with dichloromethane. The combined organic layers are washed with water, dried over MgSO4, and concentrated in vacuo to give cis-2-(2'-pentylcyclopropyl)acetic acid. |
Here is a chemical reaction formula: Reactants are:m5:Cl;m1_m6_m2_m7:C1C(=O)COC1=O;m1_m6_m2_m7:C(C)N(CC)CC;m3_m4:Cl.CN(CCCN=C=NCC)C;m3_m4:C(CCCCCCCCCCCCCCC)(=O)O, Reagents are:m1_m6_m2_m7:CN(C=O)C;m1_m6_m2_m7:CN(C1=CC=NC=C1)C, and Products are 0:OC1=C(C(OC1)=O)C(CCCCCCCCCCCCCCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring solution of 650 mg (6.5 mmol) of tetronic acid in 20 mL of dimethylformamide is added 1.0 mL (7.17 mmol) of triethylamine and 230 mg (1.88 mmol) of 4-dimethylaminopyridine at 0° C. Next, 1.50 g (7.81 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 2.0 g (7.81 mmol) of palmitic acid are added and the reaction mixture is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with ethyl acetate. The combined organic layers are washed with brine, dried over MgSO4, and concentrated in vacuo. The residue is recrystallized from pentane to give 2.0 g (91%) of 4-hydroxy-3-[1-oxohexadecyl]-2(5H)-furanone, mp 81°-83° C. |
Here is a chemical reaction formula: Reactants are:m2_m3:ClC1=C2NC=NC2=NC=N1;m2_m3:C(C)N(C(C)C)C(C)C;m1:O.NN;m0_m4:CON(C)CCCNC1=C2NC=NC2=NC=N1, Reagents are:, and Products are 0:CON(C)C(CNC1=C2NC=NC2=NC=N1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 15 ml of ethanol was dissolved 1.21 g (4.88 mmol) of the imide obtained in the above (1) and there was added 0.293 g (5.86 mmol) of hydrazine hydrate, followed by refluxing for 6 hours and cooling in an ice bath. The resulting solid was filtered off and the filtrate was concentrated to 2 ml by evaporator with a water bath at 5° C. This concentrated solution was mixed with 6 ml of n-butanol and to the mixture were added 0.528 g (3.42 mmol) of 6-chloropurine and 0.68 ml of ethyldiisopropylamine and the mixture was gently refluxed for 5 hours. This was cooled to room temperature and then the solvent was distiled off under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: chloroform/ethanol=9/1) to give 0.421 g (yield: 36%) of white crystals of N6 -[3-(N-methoxy-N-methylamino)propyl]adenine. |
Here is a chemical reaction formula: Reactants are:m1_m2:C1(=CC=CC=C1)O;m1_m2:C=CCCCCCCCCCCCCCC, Reagents are:, and Products are 0:C(CCCCCCCCCCCCCCC)C1=CC=C(C=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Phenol (376 g, 4 mol), hexadecene (α-olefin) (449 g, 2 mol) and ion exchange resin (trade-mark: Dia-ion RCP-145HD) (34 g) were charged in a reactor and stirred at 110° C. for 2 hours. The ion exchange resin was filtered off and the excessive phenol and hexadecene were distilled off under reduced pressure. After distillation under reduced pressure, mono-hexadecylphenol was obtained. The yield was 510 g. |
Here is a chemical reaction formula: Reactants are:m3_m4:S(=O)([O-])S(=O)[O-].[Na+].[Na+];m1_m2:[N+](=O)([O-])C1=C(C=CC(=C1)C(C)=O)O;m1_m2:[OH-].[Na+], Reagents are:m3_m4:O, and Products are 0:NC1=C(C=CC(=C1)C(C)=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a 300 ml three-neck flask, 5.00 g (27.6 m mole) of 2-nitro-4-acetylphenol and 75 ml of 2N-sodium hydroxide solution were placed. To the mixture solution, a solution, which 25.00 g of sodium hydrosulfite was dissolved in 75 ml to water, was added dropwise in 10 minutes. Then the mixture solution was stirred for 20 minutes at room temperature to precipitate a crystal. The crystal was filtered and recrystallized from a mixture solvent of methanol-water to obtain 1.63 g of 2-amino-4-acetylphenol (Yield: 39.1%). |
Here is a chemical reaction formula: Reactants are:m4_m10_m9:C(CCCCCCCCC)OC1=CC=C(C=C1)C=1OC2=C(N1)C=C(C=C2)C(C)=O;m6:Cl(=O)(=O)O;m3:Br[O-].[Na+];m5:Br[O-].[Na+];m1_m7:[OH-].[Na+];m2:Br(=O)(=O)O, Reagents are:m4_m10_m9:O;m4_m10_m9:O1CCOCC1;m1_m7:O;m11:O1CCOCC1;m8:O, and Products are 0:C(CCCCCCCCC)OC1=CC=C(C=C1)C=1OC2=C(N1)C=C(C=C2)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Example Compound I-51 was synthesized through the following steps: ##STR88## 1.61 g (40.3 m mole) of sodium hydroxide was dissolved in 10.7 ml of water, followed by cooling at -7.5--5° C. on ice-common salt bath. To the solution, 0.66 ml (25.6 m mole) of bromic acid was added dropwise under stirring, followed by cooling at ca. -5° C. To the mixture solution, 4.2 ml of dioxane was added dropwise under stirring to prepare sodium hypobromite solution. In a 200 ml three-neck flask, 1.50 g (3.81 m mole) of (4-decyloxyphenyl)-5-acetylbenzooxazole synthesized in Example 3, 30 ml of dioxane and 2.5 ml of water were placed, followed by keeping inner temperature below 5° C. under cooling with ice and stirring. To the mixture solution, the above-mentioned sodium hypobromite solution was added dropwise, and the reaction temperature was raised up to 45° C. and maintained for 90 minutes. After the reaction, the reaction mixture was poured into 150 ml of water. To the resultant reaction mixture, 3.2 ml of chloric acid was added to show pH=1 to precipitate a crystal. The crystal was filtered and washed with water, followed by recrystallizing from a mixture solvent of acetone-methanol to obtain 1.13 g of 2-(4-decyloxyphenyl)-5-carboxybenzooxazole (Yield: 75.0%). |
Here is a chemical reaction formula: Reactants are:m4:N1=CC=CC=C1;m1_m2_m3:NC1=C(C=CC(=C1)CCCC)O;m1_m2_m3:C(CCCCCCCCC)OC=1C=C2C=CC(=CC2=CC1)C(=O)Cl;m1_m2_m3:O1CCOCC1, Reagents are:m5:O, and Products are 0:C(CCCCCCCCC)OC=1C=C2C=CC(=CC2=CC1)C(=O)NC1=C(C=CC(=C1)CCCC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a 50 ml three-neck flask, 0.40 g (2.42 m mole) of 2-amino-4-butylphenol, 0.85 g (2.74 m mole) of 6-decyloxy-2-naphthoic acid chloride and 10 ml of dioxane were placed. To the mixture, 0.81 ml of pyridine was added dropwise under stirring at ca. 75° C. of mixture temperature. After the reaction, the reaction mixture was poured into 80 ml of water to precipitate a crystal. The crystal was filtered, washed with water and recrystallized from acetone to obtain 1.00 g of 2-(6-decyloxy-2-naphthoylamino)-4-butylphenol (Yield: 86.5%). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:OC=1C=C2C=CC(=CC2=CC1)C=1OC2=C(N1)C=C(C=C2)CCCC;m1_m2_m3_m4:C(CCCCCCC)I;m1_m2_m3_m4:[OH-].[K+];m1_m2_m3_m4:C(CCC)O, Reagents are:m5:O, and Products are 0:C(CCCCCCC)OC=1C=C2C=CC(=CC2=CC1)C=1OC2=C(N1)C=C(C=C2)CCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a 30ml round-bottom flask, 0.47 g (1.48 m mole) of 2-(6-hydroxy-2-naphthyl)-5-butylbenzooxazole, 0.43 g (1.79 m mole) of octyl iodide, 0.12 g (1.82 m mole) of potassium hydroxide and 5 ml of butanol were placed, followed by refluxing for 310 minutes. The reaction mixture was poured into water, extracted from ethyl acetate to obtain an organic layer. The organic layer was washed with water dried with mirabilite and dried under reduced pressure to obtain a resultant. The resultant was recrystallized from ethylacetate to obtain a crystal. The crystal was filtered, purified by silica gel column chromatography (eluent: toluene) and recrystallized from acetone to obtain 0.36 g of 2-(6-octyloxy-2-naphthyl)-5-butylbenzooxazole (Yield: 56.6%). ##STR190## |
Here is a chemical reaction formula: Reactants are:m3:C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)COP(=O)(O)[O-])O)C)O)F)C.[Na+];m4:C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)N)O[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O[C@@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)CN)O)O)N)O)O)N.OS(=O)(=O)O;m1:C[C@@H](C=O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H]([C@@H]1CCNC(=N)N1)NC(=O)N[C@@H](CC(C)C)C(=O)O;m2:CC(C=1C=CC(=C(C1)F)C=2C=CC=CC2)C(=O)O, Reagents are:, and Products are 0:C(C(=C)C)(=O)OCCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture was prepared by combining aprotinin 1 g.; elastatinal 0.1 g.; flurbiprofen 0.1 g.; dexamethasone sodium phosphate 0.1 g.; neomycin sulfate; and physiological saline up to 100 g. A contact lens form the crosslinked polymer of 2-hydroxyethyl methacrylate (38 percent by weight of equilibrium water) was swelled in the given solution for 24 hours. The contact lens was used for the treatment of nonhealing corneal erosions. Within a week after application the reepithalization was sped up. Extraordinary results were attained after severe etching and burning of the anterior segment of the eye. The intraocular inflammation did not develop, the cornea did not exhibit ulceration and healed with a scar to place within a month. The transparency recovered in the periphery of the cornea. |
Here is a chemical reaction formula: Reactants are:m2:C1(O)=CC(O)=CC=C1;m3:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m4:CC(C)(C1=CC=C(C=C1)OCC2CO2)C3=CC=C(C=C3)OCC4CO4;m1:C1(O)=CC(O)=CC=C1.CC(C)(C1=CC=C(C=C1)OCC2CO2)C3=CC=C(C=C3)OCC4CO4, Reagents are:m5:C1(=CC=CC=C1)C, and Products are 0:C1(O)=CC(O)=CC=C1.CCOCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A resorcinol/diglycidyl ether of bisphenol A addition product was prepared in a 3-liter reactor equipped with an agitator, thermometer and reflux condenser. The reactor was charged with about 330.3 g. resorcinol, 1500 ml. toluene and 3.0 g. triphenylphosphine. The stirred charge was heated to reflux at about 112° C. and about 654.0 g. diglycidyl ether of bisphenol A (Ciba-Geigy Araldite GY 6004) was added dropwise in about 2.5 hours. The charge was refluxed for about one hour, devolatilized at reduced pressure and about 36.0 g. amorphous silica was added to obtain a light tan resorcinol ether compound (RE4) having a 77° C. softening point, and having a 0.45 wt. % residual oxirane oxygen. |
Here is a chemical reaction formula: Reactants are:m2:C(C(=O)Cl)(=O)Cl;m3:CN(C=O)C;m1_m4:C(C)(=O)OC=1C=C(C(=O)O)C=C(C1OC(C)=O)OC(C)=O, Reagents are:m1_m4:C(Cl)Cl, and Products are 0:C(C)(=O)OC=1C=C(C(=O)Cl)C=C(C1OC(C)=O)OC(C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3,4,5-Triacetoxybenzoic acid (296.23 g, 1 mol) was slurried in a 2 L flask in CH2Cl2 (1.0 L), and oxalyl chloride (113 mL, 1.3 mol) as added, followed by slow, dropwise addition of N,N-dimethylformamide (1.5 mL). After 2 hours at RT, gas evolution had ceased, and 3,4,5-triacetoxybenzoyl chloride was isolated by evaporation under reduced pressure. |
Here is a chemical reaction formula: Reactants are:m2:B(Cl)(Cl)Cl;m1_m3:CC1=C(C2=CC=CC=C2C=C1C1=CC(=C(C=C1)C(=O)OC)OC)O, Reagents are:m4:C(Cl)Cl;m1_m3:C(Cl)Cl, and Products are 0:CC1=C(C2=CC=CC=C2C=C1C1=CC(=C(C=C1)C(=O)OC)O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cooled (-78° C.) suspension of 7.0 g of 2-methyl-3-(4'-methoxycarbonyl-3'-methoxyphenyl)-1-naphthol in 100 mL of methylene chloride was added, dropwise over 10 minutes, 26 mL of 1 M boron trichloride in methylene chloride. The resulting mixture was stirred overnight at 25° C. and then quenched with 25 mL of methanol. The solution was washed with 3×40 mL of 1 N hydrochloric acid and then 2×50 mL of saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residual oil was purified by flash chromatography (2:1 methylene chloride:hexane as eluent) to give 4.8 g of 2-methyl-3-(4'-methoxycarbonyl-3'-hydroxyphenyl)-1-naphthol as a white solid. |
Here is a chemical reaction formula: Reactants are:m1:IC1=CC(=C(C(=O)OC)C=C1)OC;m2:C(Cl)(Cl)Cl, Reagents are:m4_m3:CN(C=O)C;m4_m3:[Cu], and Products are 0:COC=1C=C(C=CC1C(=O)OC)C1=CC(=C(C=C1)C(=O)OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mechanically stirred suspension of 90 g of copper powder in 450 mL of dimethylformamide was added 90 g of methyl 4-iodo-2-methoxybenzoate (which was prepared as in Example 1). The resulting mixture was heated at reflux for 6 days and then cooled to room temperature and diluted into 1500 mL of chloroform. The mixture was filtered and the copper was washed with 2×150 mL of chloroform. The residual copper was suspended in 2 liters of water and extracted with 6×150 mL of chloroform. All the organic fractions were combined, dried and concentrated to approximately 250 mL. The concentrate was cooled to 0° C. and the precipitate filtered to give 33 g of 3,3'-dimethoxy-4,4'-bis(methoxycarbonyl)biphenyl as a pale yellow powder. Deprotection of the dimethoxy compound was accomplished with boron trichloride according to step 5 of Example 1 to yield 3,3'-dihydroxy-4,4'-bis(methoxycarbonyl)biphenyl. The structure was confirmed by NMR. |
Here is a chemical reaction formula: Reactants are:m4_m6_m5:BrC1=C(C2=CC=CC=C2C=C1)O;m4_m6_m5:C([O-])([O-])=O.[K+].[K+];m1_m2_m3:C1(=CC=CC2=CC=CC=C12)O;m1_m2_m3:BrC1=C(C2=CC=CC=C2C=C1)O;m1_m2_m3:BrNC(C)(C)C, Reagents are:m4_m6_m5:CC(=O)C, and Products are 0:BrC1=C(C2=CC=CC=C2C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1-naphthol was converted into 2-bromo-1-naphthol by reaction with a slurry of N-bromo-t-butylamine at -78° C. according to the procedure described in Pearson, Wysong, Breder, J. Org. Chem. 32, 2358 (1967). To a solution of 1 mole (crude) of the bromonaphthol in 750 mL of acetone was added 175 g of potassium carbonate. Over a 2-hous period, 95 mL of dimethylsulate was added dropwise to the mechanically stirred reaction mixture. The resulting slurry was stirred at 25° C. overnight. The solids were filtered and the solution was stripped to yield a dark brown oil. Initial purification was accomplished by vacuum distillation (80°-120° C., 0.2 Torr) followed by further purification by HPLC with hexane to yield 145 g of 2-bromo-1-methoxynaphthalene as a pale yellow oil. NMR confirmed the structure. |
Here is a chemical reaction formula: Reactants are:m3_m2:COC1=C/C(=C\2/C=C(C3=CC=CC=C3C2=O)OC)/C(=O)C4=CC=CC=C41;m1_m4:COC1=CC=C(C2=CC=CC=C12)O, Reagents are:m3_m2:[Ag]=O;m1_m4:C(Cl)(Cl)Cl, and Products are 0:COC1=CC(=C(C2=CC=CC=C12)O)C=1C=C(C2=CC=CC=C2C1O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Under an atmosphere of nitrogen, a mixture of 5.0 g of 4-methoxy-1-naphthol and 50 mL chloroform was mechanically stirred with 10.0 g silver oxide until the conversion to Russig's Blue was complete. The unreacted silver oxide was filtered and washed with chloroform. The filtrate and chloroform washings were combined and stirred with 4.9 g of 4-methoxy-1-naphthol until the solution turned gray. The solution was then concentrated to 50 mL and the resulting precipitate was filtered, washed with chloroform and dried to yield 3.18 g of 1,1'-dimethoxy-3,3'-binaphthyl-4,4'-diol as a light gray solid. The structure was confirmed by NMR. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:BrC=1C=C(N)C=CC1;m1_m2_m3_m4:[O-2].[Mg+2];m1_m2_m3_m4:C(C1=CC=CC=C1)Br, Reagents are:m1_m2_m3_m4:CN(C=O)C, and Products are 0:C(C1=CC=CC=C1)N(C1=CC(=CC=C1)Br)CC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 16 g of 3-bromoaniline, 15 g magnesium oxide and 31.8 g benzylbromide in 100 mL dry dimethylformamide was stirred for 47 hours at room temperature, under nitrogen. The precipitated magnesium salts were filtered. The filtrate was diluted with water and extracted with ether. The ether extracts were combined, washed with water and dried over anhydrous sodium sulfate. The sodium sulfate was filtered and the ether evaporated in vacuo to give a brownish solid. The brownish solid was recrystallized from isopropanol to yield 20.75 g of N,N-dibenzyl-3-bromoaniline as a white solid. The structure was confirmed by NMR. |
Here is a chemical reaction formula: Reactants are:m2_m6:C(C)(C)(C)[Li];m4_m10:Cl;m9_m3:C(=O)=O;m1_m5:BrC1=CC=C(C=C1C1=CC(=CC=C1)OC)OC, Reagents are:m4_m10:O;m9_m3:CCOCC;m7:CCOCC;m1_m5:CN(C=O)C, and Products are 0:C(=O)(O)C1=C(C=C(C=C1)OC)C1=CC=CC(=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 12.1 g of 6-bromo-3,3'-dimethoxy-biphenyl was dissolved in 100 mL of dry dimethylformamide and the resulting solution was cooled to -60° C. under nitrogen. 55 mL of 1.7 M t-butyllithium in hexanes was added over a 20-minute period. The resulting solution was transferred to another flask containing a mixture of 275 mL of ether and dry ice which effected a lot of gas evolution. The mixture was allowed to warm to room temperature over a 3-hour period during which time a white precipitate had formed. The mixture was diluted with ether and treated with dilute hydrochloric acid and water. The organic layer was separated and the solvents were removed under reduced pressure to yield a yellow oil. Hexanes were added to the oil causing a solid to precipitate out. The solids were filtered and stirred in a 60:40% ether-hexane mixture to remove impurities. The solid was filtered and dried in vacuo to yield 7.82 g of 2-carboxy-5,5'-dimethoxybiphenyl as an off-white solid. The structure was confirmed by NMR and infrared spectroscopy. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(=O)(O)C1=C(C=C(C=C1)OC)C1=CC=CC(=C1)OC, Reagents are:m1_m2:CS(=O)(=O)O, and Products are 0:COC=1C=CC=2C(C3=CC=C(C=C3C2C1)OC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 7.5 g of 2-carboxy-5,5'-dimethoxybiphenyl was dissolved in 75 mL of methanesulfonic acid to obtain a dark brown solution. The solution was stirred at room temperature for one hour, heated at 40°-50° C. for 5 hours and then cooled to room temperature. The reaction mixture was then poured onto crushed ice to form a yellow colored precipitate which was collected by filtration. The precipitate was washed with large amounts of water and then air dried to yield 6.7 g of crude 3,6-dimethoxy-9-fluorenone. Recrystallization from ethanol followed by column chromatography on silica gel using methylene chloride as the eluent yielded pure 3,6-dimethoxy-9-fluorenone. The structure was confirmed by NMR and mass spectroscopy. |
Here is a chemical reaction formula: Reactants are:m2:CO;m1:C(C1=CC=CC=C1)O, Reagents are:, and Products are 0:C1(=O)OCC2=CC=CC=C12, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The procedure described in method F is repeated, except that the methanol is replaced by 50 ml of benzyl alcohol, affording a phthalide compound of the formula ##STR19## melting point 183°-184° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3_m5:C(#N)C1=CC=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O;m1_m2_m4_m3_m5:O1CCCC=C1;m1_m2_m4_m3_m5:S(=O)(=O)(O[Si](C)(C)C)O[Si](C)(C)C, Reagents are:m1_m2_m4_m3_m5:ClCCl;m1_m2_m4_m3_m5:ClCCl, and Products are 0:O1C(CCCC1)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 3.0 g of trans-4-(4'-cyano-4-biphenylyl)cyclohexanol, 1.1 ml of 3,4-dihydro-2H-pyran in 30 ml of dichloromethane was treated at 0° C. with a solution of 0.007 g of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at 0° C. for a further 30 minutes and then washed once with sodium carbonate solution and twice with water and subsequently dried over magnesium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). Recrystallization from ethyl acetate at -20° C. gave 1.75 g of pure trans-4-(4'-cyano-4-biphenylyl)cyclohexyl tetrahydropyranyl ether. |
Here is a chemical reaction formula: Reactants are:m3:C([O-])([O-])=O.[Na+].[Na+];m1_m4_m2_m5:C(CCCCCCCC)[Mg]Br;m1_m4_m2_m5:O1C(CCCC1)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C#N;m1_m4_m2_m5:C(C)OCC, Reagents are:m1_m4_m2_m5:O1CCCC1, and Products are 0:O1C(CCCC1)O[C@@H]1CC[C@H](CC1)C1(CC=C(C=C1)C1=CC=CC=C1)C(CCCCCCCCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of nonylmagnesium bromide (8.3 mmol) in 30 ml of diethyl ether was treated at 0° C. with a solution of 1.5 g of trans-4-(4'-cyano-4-biphenylyl)cyclohexyl tetrahydropyranyl ether in 15 ml of tetrahydrofuran. The reaction mixture was heated at slight reflux overnight and then treated with dilute sodium carbonate solution. The organic phase was separated and the aqueous phase was back-extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed once with dilute sodium carbonate solution and twice with water and then dried over magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). The trans-4-(4-decanoyl-4-biphenylyl)cyclohexyl tetrahydropyranyl ether (1.8 g) obtained was used in the next step without further purification. |
Here is a chemical reaction formula: Reactants are:m3:N1=CC=CC=C1;m1_m4_m5_m2_m6:O1C(CCCC1)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CCCCCCCCCC;m1_m4_m5_m2_m6:S(=O)(=O)(O[Si](C)(C)C)O[Si](C)(C)C, Reagents are:m1_m4_m5_m2_m6:CO;m1_m4_m5_m2_m6:C(C)OCC;m1_m4_m5_m2_m6:ClCCl, and Products are 0:C(CCCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 1.2 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexyl tetrahydropyranyl ether in 40 ml of methanol and 2 ml of diethyl ether was treated with a solution of 7.3 mg of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at room temperature for 2 hours and then treated with 0.2 ml of pyridine. Subseguently, the reaction mixture was concentrated and the residue was then taken up in 50 ml of dichloromethane, washed twice with water, dried over magnesium sulfate, filtered and again concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). Recrystallization from methanol gave 0.5 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexanol. |
Here is a chemical reaction formula: Reactants are:m3:O;m1_m4:C(CCCCCCCCC)C=1C=NC(=NC1)C1=CC=C(C=C1)O;m2:BrBr, Reagents are:m1_m4:ClCCl;m5:ClCCl, and Products are 0:BrC1=C(C=CC(=C1)C1=NC=C(C=N1)CCCCCCCCCC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 5 g of 4-(5-decyl-2-pyrimidinyl)phenol in 50 ml of dichloromethane was treated at 0° C. while gassing with argon with a solution of 2.6 g of bromine in 50 ml of dichloromethane. The reaction mixture was stirred for a further 2 hours and then treated with water. The organic phase was separated and the aqueous phase was back-extracted three times with 50 ml of dichloromethane each time. The combined organic phases were washed with water, sodium hydrogen carbonate solution and again with water, dried over magnesium sulfate, filtered and subsequently concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 4:1). Recrystallization from hexane gave 4.8 g of 2-bromo-4-(5-decyl-2-pyrimidinyl)phenol. |
Here is a chemical reaction formula: Reactants are:m2_m5:C[C@H](CCCCCC)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C1CCC(CC1)=O;m1_m4:[BH4-].[Na+];m3:Cl, Reagents are:m2_m5:COCCOC;m1_m4:COCCOC, and Products are 0:C[C@H](CCCCCC)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of 0.14 g of sodium borohydride in 10 ml of 1,2-dimethoxyethane was treated at 0° C. with a solution of 4-(4'-[(R)-2-octyl]oxycarbonyl-4-biphenylyl)cyclohexanone in 10 ml of 1,2-dimethoxyethane. The reaction mixture was stirred at room temperature for a further 30 minutes and then treated with 25% hydrochloric acid. The reaction mixture was extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed with sodium hydrogen carbonate solution and several times with water and subsequently dried over magnesium sulfate, filtered and concentrated. The residue was recrystallized twice from hexane and gave 0.8 g of trans-4-(4'-[(R)-2-octyl]oxycarbonyl 4-biphenylyl)cyclohexanol. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)OC(=O)N=C1SC(CN1C1=CC(=CC=C1)C(F)(F)F)CBr;m1_m2_m3:CC(C)([O-])C.[K+], Reagents are:m1_m2_m3:C(C)(C)(C)O, and Products are 0:C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-bromomethylthiazolidine (0.7 g) and potassium t-butoxide (0.25 g) in t-butanol (30 ml) was refluxed for 5 hours. After removal of the solvent under reduced pressure, the concentrated residue was extracted with chlorofom (100 ml), washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 0.36 g of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (Compound No. 1). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)OC(=O)N=C1SC(CN1C1=CC(=CC=C1)C(F)(F)F)=C;m1_m2_m3:C[O-].[Na+], Reagents are:m1_m2_m3:C(C)O, and Products are 0:C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-ethoxycarbonylimino-3-(3-tri-fluoromethylphenyl)-5-methylenethiazolidine (2.0 g) and sodium methoxide (28 % methanolic solution; 1.2 g) in ethanol (50 ml) was refluxed for 30 minutes. After removal of the solvent under reduced pressure, the concentrated residue was extracted with chlorofom (200 ml), washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 1.6 g of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-methyl-thiazoline (Compound No. 1). |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)CC;m1_m2_m4_m3:C(C)N(CC)CC;m1_m2_m4_m3:C(CC(C)C)(=O)Cl, Reagents are:m1_m2_m4_m3:C(Cl)(Cl)Cl, and Products are 0:C(CC(C)C)(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 2-imino-3-(3-trifluoromethylphenyl)-5-ethylthiazoline (0.5 g) and triethylamine (0.6 g) in chloroform (30 ml), isovaleryl chloride (0.8 g) was dropwise added under stirring at room temperature, and stirring was continued for 2 hours. After removal of the solvent under reduced pressure, the concentrated residue was extracted with ethyl acetate (100 ml), washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 0.2 g of 2-isovalerylimino-3-(3-trifluoromethylphenyl)-5-ethylthiazoline (Compound No. 16). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:Cl.N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C;m1_m2_m3_m4_m5:C(C)N(CC)CC;m1_m2_m3_m4_m5:Cl.C(C)N=C=NCCCN(C)C;m1_m2_m3_m4_m5:FC(C(=O)O)F, Reagents are:m1_m2_m3_m4_m5:C(Cl)(Cl)Cl, and Products are 0:FC(C(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline hydrochloride (0.42 g), triethylamine (2.2 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.8 g) and difluoroacetic acid (0.75 g) in chloroform (10 ml) was refluxed for 8 hours. The residue was washed with aqueous hydrochloric acid and aqueous potassium carbonate and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 2-difluoroacetylimino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (Compound No. 63) (0.3 g). m.p., 117.9° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C;m1_m2_m3:C[O-].[Na+], Reagents are:m1_m2_m3:CO, and Products are 0:COC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (1.0 g) and sodium methoxide (28 % methanolic solution; 0.6 g) in methanol (30 ml) was refluxed for 10 hours. After removal of the solvent, the residue was extracted with chloroform (100 ml), washed with water and dried over anhydrous magnesium. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 0.8 g of 2-methoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (Compound No. 3). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)NC(=O)N=C1SC(CN1C1=CC(=CC=C1)C(F)(F)F)=C;m1_m2_m3:C[O-].[Na+], Reagents are:m1_m2_m3:CO, and Products are 0:C(C)NC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-(N-ethylcarbamoylimino)-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine (0.2 g) and sodium methoxide (28 % methanolic solution; 0.2 g) in methanol (30 ml) was refluxed for 10 hours. After removal of the solvent, the residue was extracted with chloroform (100 ml), washed with water and dried over anhydrous magnesium. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 0.1 g of 2-(N-ethylcarbamoylimino)-3-(3-trifluoromethylphenyl)-5-methylthiazoline (Compound No. 44). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)OC(=O)N=C1SCCN1C1=CC(=CC=C1)C(F)(F)F;m1_m2_m3:BrN1C(CCC1=O)=O, Reagents are:m1_m2_m3:C(Cl)(Cl)Cl, and Products are 0:C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)Br, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)thiazolidine (1.6 g) and N-bromosuccinimide (2 g) in chloroform (50 ml) was refluxed for 10 hours. After cooling, the reaction mixture was washed with an aqueous sodium sulfite solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 0.9 g of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-bromothiazoline (Compound No. 30). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)OC(=O)N=C1SC=CN1C1=CC(=CC=C1)C(F)(F)F;m1_m2_m3:IN1C(CCC1=O)=O, Reagents are:m1_m2_m3:C(Cl)(Cl)Cl, and Products are 0:C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)I, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)thiazoline (0.5 g) and N-iodosuccinimide (0.4 g) in chloroform (30 ml) was refluxed for 20 hours. After cooling, the reaction mixture was washed with an aqueous sodium sulfite solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 0.1 of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-iodothiazoline (Compound No. 42). |
Here is a chemical reaction formula: Reactants are:m1_m2:FC(C=1C=C(N)C=CC1)(F)F;m1_m2:C(C#C)Br, Reagents are:, and Products are 0:C(C#C)NC1=CC(=CC=C1)C(F)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 3-trifluoromethylaniline (30 g) ad propargyl bromide (12 g) was stirred at 80° C. for 3 hours, followed by filtration of the reaction mixture. The filtrate was subjected to column chromatography to give N-propargyl-3-trifluoromethylaniline (7 g). A solution of N-propargyl-3-trifluoromethylaniline thus obtained (5.1 g) and ethoxycarbonyl isothiocyalate (3.7 g) in tetrahydrofuran (100 ml) was stirred at room temperature for 8 hours, and the solvent was removed under reduced pressure. The concentrated residue was extracted with chloroform (200 ml), washed with water and dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was subjected to column chromatography to give 5.7 g of 2 -ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine (Compound (i)). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)OC(=O)N=C1SC(CN1C1=CC(=CC=C1)C(F)(F)F)CBr;m1_m2_m3:CC(C)([O-])C.[K+], Reagents are:m1_m2_m3:C(C)(C)(C)O, and Products are 0:C(C)OC(=O)N=C1SC(CN1C1=CC(=CC=C1)C(F)(F)F)=C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-bromomethylthiazolidine (0.7 g) and potassium t-butoxide (0.25 g) in t-butanol (30 ml) was refluxed for 5 hours, and the solvent was distilled off under reduced pressure. The residue was extracted with chloroform (100 ml), washed with water and dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was subjected to column chromatography to give 0.25 g of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine (Compound (i)). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C;m1_m2_m3:Cl, Reagents are:m1_m2_m3:C(C)O.O, and Products are 0:N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2-(acetylimino)-3-(3-trifluoromethylphenyl)-5-methylthiazoline (1 g) and hydrochloric acid (38 %, 4 ml) in ethanol-water (1:2, 15 ml) was refluxed for 3 hours. Ethanol was removed by distillation under reduced pressure, and the residue was neutralized with potassium carbonate, extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to give 0.4 g of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (Compound (xi)). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)Br;m1_m2_m3_m4:C(CCC)[SnH](CCCC)CCCC;m1_m2_m3_m4:C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O, Reagents are:m1_m2_m3_m4:O1CCCC1, and Products are 0:C(C)OC(=O)N=C1SC=CN1C1=CC(=CC=C1)C(F)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-bromothiazoline (4.7 g), tributyltin hydride (6.9 g) and a catalytic amount of benzoyl peroxide in tetrahydrofuran (100 ml) was refluxed for 10 hours. The solvent was removed by distillation, and the residue was washed with hexane. Recrystallization from a mixture of hexane and ethanol gave 2.85 g of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)thiazoline (Compound (xii)). |