INSTRUCTION
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Here is a chemical reaction formula: Reactants are:m1:C(#N)C1=CC=C(C=C1)O;m3:C([O-])([O-])=O.[K+].[K+];m2:ClC(C(=O)OC)(F)F;m4:C(C)(=O)OCC, Reagents are:m5:CN(C)C=O, and Products are 0:FC(OC1=CC=C(C#N)C=C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Cyanophenol (0.12 G, 1.0 mmol, Aldrich), methyl chlorodifluoroacetate (0.29 g, 2.0 mmol, Aldrich) and potassium carbonate (0.29 g, 2.1 mmol) were combined in dry DMF (0.5 mL) under an argon atmosphere. After stirring at 75°-80° C. for 0.3 h, the mixture was cooled to RT, ethyl acetate (20 mL) was added and the organic layer was washed twice with 10% NaOH. The organic extract was dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 20% ether/hexanes) to provide the title compound as a colorless solid (0.09 g, 53%). mp 34°-35° C. |
Here is a chemical reaction formula: Reactants are:m1:[N+](=O)([O-])C1=CC=C(C=C1)O;m4:C(C)(=O)OCC;m2:ClC(C(=O)OC)(F)F;m3:C([O-])([O-])=O.[K+].[K+], Reagents are:m5:CN(C)C=O, and Products are 0:FC(OC1=CC=C(C=C1)[N+](=O)[O-])F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Nitrophenol (0.14 g, 1.0 mmol, Aldrich), methyl chlorodifluoroacetate (0.29 g, 2.0 mmol, Aldrich) and potassium carbonate (0.29 g, 2.1 mmol) were combined in dry DMF (0.5 mL) under an argon atmosphere. After stirring at 95°-100° C. for 0.5 h, the mixture was cooled to RT, ethyl acetate (20 mL) was added and the organic layer was washed three times with 10% NaOH. The organic extract was dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 20% ether/hexanes) to provide the title compound as a white solid (0.12 g, 65%). mp 33°-35° C. |
Here is a chemical reaction formula: Reactants are:m2:ClC(C(=O)OC)(F)F;m1:OC=1C=C(C=O)C=CC1O;m3:C([O-])([O-])=O.[K+].[K+], Reagents are:m4:CN(C)C=O, and Products are 0:FC(OC1=C(C=C(C=O)C=C1)O)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3,4-Dihydroxybenzaldehyde (0.50 g, 3.62 mmol, Aldrich), methyl chlorodifluoroacetate (0.52 g, 3.62 mmol, Aldrich) and potassium carbonate (0.50 g, 3.62 mmol) were combined in DMF (5.0 mL) under an argon atmosphere. After stirring at 60°-65° C. for 3 h, DMF was removed in vacuo and the residue was partioned between aqueous 3N HCl and ether. The aqueous layer was extracted three times with ether. The combined organic extracts were washed with water, with brine, were dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes) to provide the title compound as a white solid (0.20 g, 38%). mp 83°-85° C. |
Here is a chemical reaction formula: Reactants are:m4_m5:ClC(C(=O)OC)(F)F;m4_m5:C([O-])([O-])=O.[K+].[K+];m2:ClC(C(=O)OC)(F)F;m1:C(C)(=O)N1CCC2=CC(=C(C=C12)Br)O;m3:C([O-])([O-])=O.[K+].[K+], Reagents are:m6:CN(C=O)C, and Products are 0:C(C)(=O)N1CCC2=CC(=C(C=C12)Br)OC(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1-Acetyl-6-bromo-5-hydroxyindoline (2 g, 7.8 mmol), methyl 2-chloro-2,2-difluoroacetate (0.82 ml, 7.8 mmol) and potassium carbonate (1.08 g, 7.8 mmol) were suspended in N,N-dimethylformamide (20 mL) under an argon atmosphere and placed in a 65° C. oil bath. After 3 hr, additional methyl 2-chloro-2,2-difluoroacetate (0.3 ml, 2.8 mmol) and potassium carbonate (0.3 g, 2.2 mmol) was added and heated for 18 hr. The solvent was then removed in vacuo and the residue was partitioned between cold 3N HCl and ether. The aqueous layer was extracted three times with ether, the combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated. The solid was purified by flash chromatography (2% MeOH/CH2Cl2) to provide the title compound as a white solid |
Here is a chemical reaction formula: Reactants are:m5:C1(=CC=CC=C1)C;m3:C([O-])([O-])=O.[K+].[K+];m4:CCCCCCCCCCCCC;m2:IC=1C=C(CCC(=O)OCC)C=CC1;m1:NC1=CC(=C(C=C1)C)C, Reagents are:m6:O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cu+2], and Products are 0:C(C)OC(=O)CCC=1C=C(C=CC1)N(C1=CC(=C(C=C1)C)C)C1=CC(=CC=C1)CCC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a 100 ml-volume flask, 6 g of 3,4-xylidine, 34 g of ethyl 3-iododihydrocinnamate, 19 g of potassium carbonate, 5 g of copper sulfate pentahydrate and 20 ml of n-tridecane were placed, and the mixture was reacted under heating at 230° C. for 10 hours in a nitrogen stream. After the reaction, the system was cooled to room temperature, the reaction mixture was dissolved in 50 ml of toluene, insoluble matters were filtered, and the filtrate was purified by silica gel column chromatography using toluene to obtain 20 g of N, N-bis[3-(2-ethoxycarbonylethyl)phenyl]-3,4-xylidine as an oily substance. The IR spectrum of the product is shown in FIG. 1. |
Here is a chemical reaction formula: Reactants are:m5:C1(=CC=CC=C1)C;m3:C([O-])([O-])=O.[K+].[K+];m2:IC=1C=C(CCC(=O)OCC)C=CC1;m1:C1(=CC=CC=C1)NC1=CC=C(C=C1)C1=CC=C(NC2=CC=CC=C2)C=C1;m4:CCCCCCCCCCCCC, Reagents are:m6:O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cu+2], and Products are 0:C1(=CC=CC=C1)N(C1=CC=C(C=C1)C1=CC=C(C=C1)N(C1=CC(=CC=C1)CCC(=O)OCC)C1=CC=CC=C1)C1=CC(=CC=C1)CCC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a 100 ml-volume flask, 10.77 g of N,N'-diphenylbenzidine, 23.0 g of ethyl 3-iododihydrocinnamate, 11.61 g of potassium carbonate, 1.0 g of copper sulfate pentahydrate and 20 ml of n-tridecane were placed, and the mixture was reacted under heating at 230° C. for one hour in a nitrogen stream. After the reaction, the system was cooled to room temperature, the reaction mixture was dissolved in 50 ml of toluene, insoluble matters were filtered and the filtrate was purified by silica gel column chromatography using toluene to obtain 19.6 g of N,N'-diphenyl-N,N'-bis[3-(2-ethoxycarbonylethyl)phenyl]-[1,1'-biphenyl]-4,4'-diamine as an oily substance. The IR spectrum of the product is shown in FIG. 2. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:OC1=CC=C(C=O)C=C1;m1_m2_m3_m4:BrCCCBr, Reagents are:m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+];m1_m2_m3_m4:CN(C)C=O, and Products are 0:C(=O)C1=CC=C(OCCCOC2=CC=C(C=C2)C=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 10.0 g of 4-hydroxybenzaldehyde and 8.3 g of 1,3-dibromopropane were reacted for 24 hours in 6.2 g of potassium carbonate solution in 100 ml of DMF under reflux. The reaction mixture was poured into cold distilled water to obtain a precipitate. After filtration and vacuum drying the precipitate, the resultant was recrystallized in ethanol to obtain the white product (XII-1). The product yield was 76%. |
Here is a chemical reaction formula: Reactants are:m3:C(#CCCCC)[Cu];m4:C(C)(C)(C)[C@@H]1C(=C(C(C1)=O)SCCCCCC(=O)OC)O[SiH](C)C;m2:C(C)(C)(C)[Li];m5:C(C(C)C)(=O)OC(C(C)C)=O;m1:I\C=C\[C@H](C[C@@H](CCCC)C)O[Si](C)(C)C(C)(C)C, Reagents are:m6:CN(P(N(C)C)N(C)C)C, and Products are 0:COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@@H](CCCC)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C(C)C)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using as the materials and reagents (1E,3S,5R)-1-iodo-3-(tert-butyldimethylsiloxy)-5-methyl-1-nonene (476 mg, 1.2 mmol), tert-butyllithium (1.54 mol/l, 1.56 ml, 2.4 mmol), 174 mg of 1-hexynylcopper, hexamethylphosphorous triamide (436 μl), (4R)-tert-butyldimethylsiloxy-2-(5-methoxycarbonylpentylthio)-2-cyclopenten-1-one (373 mg, 1 mmol), and isobutyric anhydride (448 μl), the same procedure was performed as in Example 1 to obtain methyl(11R,12S,13E,15S,17R)-9-isobutyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (466 mg, 65%). |
Here is a chemical reaction formula: Reactants are:m1:N1=CC=CC=C1.F;m2:COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@@H](CCCC)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C(C)C)=O)=O, Reagents are:, and Products are 0:COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@@H](CCCC)C)O)O)OC(C(C)C)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using as the material and reagent a hydrogen fluoride-pyridine solution (0.6 ml) and methyl(11R,12S,13E,15S,17R)-9-isobutyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (466 mg), the same procedure as in Example 2 was performed to obtain methyl(11R,12S,13E,15S,17R)-9-isobutyryloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (192 mg, 64%). |
Here is a chemical reaction formula: Reactants are:m1:N1=CC=CC=C1.F;m2:COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@@H](CCCC)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C(C)(C)C)=O)=O, Reagents are:, and Products are 0:COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@@H](CCCC)C)O)O)OC(C(C)(C)C)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using as the material and reagent a hydrogen fluoride-pyridine solution (0.7 ml) and methyl(11R,12S,13E,15S,17R)-9-pivaloyloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (564 mg), the same procedure was performed as in Example 2 was performed to obtain methyl(11R,13E,15S,17R)-9-pivaloyloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (211 mg, 55%). |
Here is a chemical reaction formula: Reactants are:m1:N1=CC=CC=C1.F;m2:C(CCC)(=O)OC1=C(SCCCCCC(=O)OCCCC)[C@H]([C@@H](C1)O[Si](C)(C)C(C)(C)C)\C=C\[C@H](C[C@@H](CCCC)C)O[Si](C)(C)C(C)(C)C, Reagents are:, and Products are 0:C(CCC)(=O)OC1=C(SCCCCCC(=O)OCCCC)[C@H]([C@@H](C1)O)\C=C\[C@H](C[C@@H](CCCC)C)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using as the material and reagent a hydrogen fluoride-pyridine solution (0.2 ml) and butyl (11R,12S,13E,15S,17R)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (138 mg), the same procedure as in Example 2 was performed to obtain butyl (11R,12S,13E,15S,17R)-9-butyryloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (69 mg, 72%). |
Here is a chemical reaction formula: Reactants are:m1:I\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C;m3:C(#CCCCC)[Cu];m5:C(C1=CC=CC=C1)(=O)OC(C1=CC=CC=C1)=O;m4:C(C)(C)(C)[C@@H]1C(=C(C(C1)=O)SCCCCCC(=O)OC)O[SiH](C)C;m2:C(C)(C)(C)[Li], Reagents are:m6:CN(P(N(C)C)N(C)C)C, and Products are 0:COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C1=CC=CC=C1)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using as the materials and reagents (1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-1-octene (442 mg, 1.2 mmol), tert-butyllithium (1.54 mol/l, 1.56 ml, 2.4 mmol), 1-hexynylcopper (174 mg), hexamethylphosphorous triamide (436 μl), (4R)-tert-butyldimethylsiloxy-2-(5-methoxycarbonyl-pentylthio)-2-cyclopenten-1-one (373 mg, 1.0 mmol), and benzoic anhydride (661 mg), the same procedure was performed as in Example 1 to obtain methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate (239 mg, 33%). |
Here is a chemical reaction formula: Reactants are:m2:COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C1=CC=CC=C1)=O)=O;m1:N1=CC=CC=C1.F, Reagents are:, and Products are 0:C(C1=CC=CC=C1)(=O)OC1=C(SCCCCCC(=O)OC)[C@H]([C@@H](C1)O)\C=C\[C@H](CCCCC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using as the material and reagent a hydrogen fluoride-pyridine solution (0.3 ml) and methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate (239 mg), the same procedure as in Example 2 was performed to obtain methyl(11R,13E,15S)-9-benzoyloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienoate (144 mg, 86%). |
Here is a chemical reaction formula: Reactants are:m1:N1=CC=CC=C1.F;m2:COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@@H](CCCC)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C1=CC=CC=C1)=O)=O, Reagents are:, and Products are 0:COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@@H](CCCC)C)O)O)OC(C1=CC=CC=C1)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using as the material and reagent a hydrogen fluoride-pyridine solution (0.7 ml) and methyl(11R,12S,13E,15S,17R)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (734 mg), the same procedure as in Example 2 was performed to obtain methyl(11R,12S,13E,15S,17R)-9-benzoyloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (141 mg, 28%) |
Here is a chemical reaction formula: Reactants are:m1:N1=CC=CC=C1.F;m2:COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC([C@@H](NC(=O)OCC1=CC=CC=C1)CC1=CC=CC=C1)=O)=O, Reagents are:, and Products are 0:COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](CCCCC)O)O)OC([C@@H](NC(=O)OCC1=CC=CC=C1)CC1=CC=CC=C1)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using as the material and reagent a hydrogen fluoride-pyridine solution (0.3 ml) and methyl(11R,12S,13E,15S)-9-(N-benzyloxycarbonylphenylalanyloxy)-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate (140 mg), methyl(11R,12S,13E,15S)-9-(N-benzyloxycarbonylphenylalanyloxy)-11,15-dihydroxy-7-thiaprosta-8,13-dienoate (53 mg, 51%) was obtained. |
Here is a chemical reaction formula: Reactants are:m1:N1=CC=CC=C1.F;m2:C(CCC)(=O)OC1=C(SCCCCCC(=O)OC)[C@H]([C@@H](C1)O[Si](C)(C)C(C)(C)C)\C=C\C(C(CCCCC)(C)C)O, Reagents are:, and Products are 0:C(CCC)(=O)OC1=C(SCCCCCC(=O)OC)[C@H]([C@@H](C1)O)\C=C\C(C(CCCCC)(C)C)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using as the materials a hydrogen fluoride-pyridine solution (0.25 ml) and methyl(11R,12S,13E)-9-butyryloxy-11-tert-butyldimethylsiloxy-15-hydroxy-16,16,20-trimethyl-7-thiaprosta-8,13-dienoate (100 mg), the same procedure as in Example 2 was performed to separately obtain two stereoisomers of methyl(11R,12S,13E)-9-butyryloxy-11,15-dihydroxy-16,16,20-trimethyl-7-thiaprosta-8,13-dienoate different at the 15-position. (Low polarity compound: 26 mg, 33%; high polarity compound: 28 mg, 35%) |
Here is a chemical reaction formula: Reactants are:m2_m6:ClC(=O)OCC(C)C;m7_m1:C(CCC)(=O)OC1=C(SCCCCCC(=O)O)[C@H]([C@@H](C1)O[Si](C)(C)C(C)(C)C)\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C;m3:[OH-].[NH4+];m4:Cl, Reagents are:m2_m6:C(C)N(CC)CC;m5:C(C)(=O)OCC;m7_m1:C(Cl)Cl, and Products are 0:C(CCC)(=O)OC1=C(SCCCCCC(=O)N)[C@H]([C@@H](C1)O[Si](C)(C)C(C)(C)C)\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A methylene chloride (3 ml) solution of (11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoic acid (201 mg) was cooled to -40° C., then isobutyl chloroformate (47 μl) and triethylamine (63 μl) were added to the solution which was then stirred as is at -40° C. for 30 minutes. Further 1 ml of 30% ammonium hydroxide solution was added and the mixture was stirred overnight while raising the temperature to room temperature. The reaction solution was diluted by ethyl acetate then was neutralized by dilute hydrochloric acid. The desired substance was extracted from the mixture by ethyl acetate and extract was successively washed by saturated sodium hydrogen carbonate and saturated sodium chloride solution. This solution was concentrated under reduced pressure, then was purified by silica gel column chromatography (45% ethyl acetate/hexane) to obtain (11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienamide (169 mg, 84%). |
Here is a chemical reaction formula: Reactants are:m2:C(CCC)(=O)OC1=C(SCCCCCC(=O)N)[C@H]([C@@H](C1)O[Si](C)(C)C(C)(C)C)\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C;m1:N1=CC=CC=C1.F, Reagents are:, and Products are 0:C(CCC)(=O)OC1=C(SCCCCCC(=O)N)[C@H]([C@@H](C1)O)\C=C\[C@H](CCCCC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using as the material and reagent a hydrogen fluoride-pyridine solution (0.2 ml) and (11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienamide (169 mg), the same procedure was followed as in Example 2 to obtain (11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienamide (101 mg, 91%). |
Here is a chemical reaction formula: Reactants are:m2:C(C)N(C(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(CCC)=O)=O)CC;m1:N1=CC=CC=C1.F, Reagents are:, and Products are 0:C(C)N(C(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](CCCCC)O)O)OC(CCC)=O)=O)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using as the material and reagent a hydrogen fluoride-pyridine solution (0.2 ml) and N,N-diethyl(11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienamide (169 mg), the same procedure as in Example 2 was performed to obtain N,N-diethyl(11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienamide (101 mg, 78%). |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:CC(C)(C(=C(C(C)(C)C)C1=CC=C(C=C1)[N+](=O)[O-])C1=CC=C(C=C1)[N+](=O)[O-])C;m1_m2_m4_m3:C1=CCCCC1, Reagents are:m1_m2_m4_m3:C1CCOC1;m1_m2_m4_m3:[Pd], and Products are 0:CC(C)(C(=C(C(C)(C)C)C1=CC=C(C=C1)N)C1=CC=C(C=C1)[N+](=O)[O-])C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 0.62 g 2,2,5,5-tetramethyl-3,4-di(4-nitrophenyl)hex-3-ene,2.6 g cyclohexene and 1.4 g 10% Pd/C in THF was refluxed for 2 hrs. The Pd/C was removed by filtration and the residue after evaporation of the solvent was purified by chromatography on silica gel (25% CH2Cl2 -hexane) to give 0.285 g (50%) 2,2,5,5-tetramethyl-3-(4-nitrophenyl)-4-(4-aminophenyl)hex-3-ene: 1H NMR (CDCl3): δ0.66 (s, 8H), 0.70 (s, 8H), 3.61 (s, 2H), 6.61-6.63 (d, 2H), 7.30-7.34 (d, 2H), 8.12-8.14 (d, 2H): 13C NMR (CDCl3): δ32.81, 32.84, 37.59, 38.16, 113.58, 121.93, 131.34, 131.48, 133.12, 143.78, 144.58, 146.22, 146.88, 152.11. |
Here is a chemical reaction formula: Reactants are:m1:ClC=1C=C(C=CC1Cl)CCCCN;m3_m4_m0:C(C)(=O)NC1(CCN(CC1)C(CC(CN)C1=CC(=C(C=C1)Cl)Cl)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1;m3_m4_m0:C(C1=CC=CC=C1)=O;m2:FC(C=1C=C(C=O)C=C(C1)C(F)(F)F)(F)F, Reagents are:, and Products are 0:C(C)(=O)NC1(CCN(CC1)C(CC(CNCC1=CC=CC=C1)C1=CC(=C(C=C1)Cl)Cl)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using a procedure similar to that described in Example 1, except replacing the (3,4-dichlorophenyl)butylamine and the 3,5-bis-(trifluoromethyl)benzaldehyde used therein with 4-(4-acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-[3,5-bis(trifluoromethyl)benzyl]butylamine and benzaldehyde, respectively, the title compound was prepared; mp 65°-67° C.; NMR: 7.85 (s,1), 7.75 (s,1), 7.65 (s,1), 7.45 (s,1), 7.40-6.95 (broad m,10), 3.85 (d,1, J=15.9), 3.65 (d,1 J=13.6) 3.56 (d,1, J=15.9), 3.42 (d,1, J=13.6), 3.05 (m, 1), 2.75-2.40 (m,4), 2.35-2.18 (m, 2), 2.18-1.95 (m,4), 1.85 (s,3); MS: m/z=750(M+1,100%). Analysis for C39H39Cl2F6N3O: Calculated: C, 61.10; H, 5.13; N, 5.48; Found: C, 61.12; H, 5.34; N, 5.65. |
Here is a chemical reaction formula: Reactants are:m4:C(C)(=O)OC(C)=O;m1_m5_m2_m3:C(C)(=O)NC1(CCN(CC1)C(CC(CN)C1=CC(=C(C=C1)Cl)Cl)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1;m1_m5_m2_m3:C(C)(=O)OC(C)=O;m1_m5_m2_m3:C(C)(C)N(CC)C(C)C, Reagents are:m7_m8_m9:Cl;m7_m8_m9:ClCCl;m7_m8_m9:O;m1_m5_m2_m3:O1CCCC1;m6:CN(C1=CC=NC=C1)C, and Products are 0:C(C)(=O)NC1(CCN(CC1)C(CC(CNC(C)=O)C1=CC(=C(C=C1)Cl)Cl)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 4-(4-acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-[3,5-bis(trifluoromethyl)benzyl]butylamine (0.4 g) in tetrahydrofuran (4 mL) was added acetic anhydride (0.085 mL) and diisopropylethylamine (0.32 mL). After 2 hours at room temperature 4-dimethylaminopyridine (7 mg) was added and the mixture was stirred overnight. Additional acetic anhydride (0.06 mL) was added and the reaction mixture was brought to reflux for 3 hours. The mixture was allowed to cool and diluted with aqueous hydrochloric acid (1N, 3 mL), dichloromethane (5 mL), and water (5 mL). The phases were separated and the aqueous layer was extracted with dichloromethane (2×5 mL). The combined organic phases were washed (brine), dried, and evaporated to afford crude product, which was purified by chromatography with dichloromethane:methanol (15:1) as eluent, to afford the title compound as a white solid; mp 115°-117° C.; NMR (d6 -DMSO-trifluoroacetic acid): 8.0-7.5 (m,5), 7.45-7.2 (m,6), 4.80-4.45 (m,2), 3.45 (m,2), 3.1 (m,4), 2.67 (m,1), 2.67 (m,2), 2.55 (s,3), 1.95 (s,3), 2.0 (broad m,5); MS: m/z=702(M+1,100%). Analysis for C34H35Cl2F6N3O2.1.50 H2O: Calculated: C, 55.97; H, 5.25; N, 5.76; Found: C, 55.91; H, 5.11; N, 5.76. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:OC1=NC(NC(=C1)O)(N)C;m1_m2_m3:[O-]CC.[Na+];m1_m2_m3:[Na];m4_m5:Cl.C(C)(=N)N;m4_m5:C(CC(=O)OCC)(=O)OCC, Reagents are:m6:C(C)O, and Products are 0:OC1=NC(=NC(=C1)O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The first intermediate, 4,6-dihydroxy-2-methylpyrimidinamine, is synthesized by preparing sodium ethoxide in situ from sodium and an hydrous ethanol under a nitrogen blanket. Acetamidine hydrochloride and diethyl malonate are added and the reaction mixture heated to boiling for 2 to 5 hours to afford 4,6-dihydroxy-2-methylpyrimidine. |
Here is a chemical reaction formula: Reactants are:m1_m2:OS(=O)(=O)O.O=S(=O)=O;m1_m2:C1(=CC=CC=C1)O, Reagents are:, and Products are 0:C1=CC(=CC=C1O)S(=O)(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 440 parts of 66% oleum are added slowly at from 60° to 70° C. to 500 parts of melted phenol, and the mixture is subsequently sulfonated at 100° C. for 1 hour. The phenolsulfonic acid formed is then slowly heated at from 160° to 165° C. in a vacuum of from about 11 to 13 mm, so that only a little phenol distils off, and is maintained at this temperature until 1 g of the condensation product neutralizes 3.5 to 3.7 cm3 of 1N sodium hydroxide solution against Congo red. 90 to 100 parts of phenol are added to the condensation product thus formed, and, after the phenol has been mixed in thoroughly, the reaction mixture is again placed slowly under vacuum and heated at 165° C. in a vacuum until 1 g of the condensation product neutralizes only 2.7 to 2.5 cm3 of 1-normal sodium hydroxide solution against Congo red. 100 parts of this condensation product are melted carefully with 54 parts of 30% sodium hydroxide solution, 22 parts of 37% formaldehyde solution are added, and the mixture is then subjected to condensation at from 100° to 105° C. (about 6 hours) until a sample diluted with a little water remains clear down to a pH of 3.5 when acidified with dilute sulfuric acid. |
Here is a chemical reaction formula: Reactants are:m1:OS(=O)(=O)O.O=S(=O)=O;m2:C1(=CC=CC=C1)O, Reagents are:, and Products are 0:C1=CC(=CC=C1O)S(=O)(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 478 parts of 20% oleum are added with stirring to 500 parts of melted phenol, with cooling to ensure that the temperature does not exceed 70° C. The mixture is then sulfonated at 105° C. for 1 hour. The phenolsulfonic acid formed is heated slowly at from 150° to 155° C. under reduced pressure of 11 to 13 torr, and this temperature is maintained until 1 g of the condensation product neutralizes 3.8 to 4.0 cm3 of 1-normal sodium hydroxide solution against Congo red. 100 parts of the hydroxyphenyl sulfone-(poly)hydroxyphenyl sulfone monosulfonic acid obtained are melted at 90° C. with 42 parts of water, and 14.4 parts of urea are added. After cooling to 55° C., 38.4 parts of 37% formaldehyde are added dropwise in the course of 2 hours and stirring is continued for about 4 hours until the condensation product gives a clear solution in water. |
Here is a chemical reaction formula: Reactants are:m3:O;m1_m4_m2:[Na];m1_m4_m2:FC1=CC=C(C=C1)[N+](=O)[O-];m1_m4_m2:FC(CO)(F)F, Reagents are:, and Products are 0:FC(COC1=CC=C(C=C1)[N+](=O)[O-])(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Under a nitrogen atmosphere, 10.1 g (0.44 mol) of sodium was dissolved in 200 ml of 2,2,2-trifluoro ethanol in 300 ml of a three-necked flask, to which 40 ml (0.38 mol) of p-fluoronitro benzene was dropped and refluxed for 4 hours. After cooling to a room temperature, water was poured (about 1 liter), and precipitated solids were washed with water and dried, to obtain p-(2,2,2-trifluoroethoxy) nitrobenzene (yield: 62%; and melting point: 76.5° C.). |
Here is a chemical reaction formula: Reactants are:m5:O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3;m6:[O-2].[O-2].[Ti+4];m4:[O-2].[O-2].[Ti+4];m3:O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3;m1_m2:[O-2].[O-2].[Ti+4];m1_m2:P(O)(O)(O)=O, Reagents are:, and Products are 0:[O-]P([O-])(=O)OP(=O)([O-])[O-].[Ti+4], please give me the reaction condition of this formula. | The condition of this chemical reaction is: The method of the present invention generally involves the mixture of titanium dioxide and hot concentrated phosphoric acid in a reaction vessel. The reaction mixture has a phosphorus pentoxide to titanium dioxide mole ratio greater than one. Preferably, the phosphorus pentoxide to titanium dioxide mole ratio is about 1.06 or more, and most preferably about 1.20 to about 1.25. The reactants are thoroughly mixed and heated at temperatures of about 400° C. to about 500° C. to produce a fine titanium pyrophosphate powder having a significantly higher fines yield over conventional titanium pyrophosphate processes. The fines yield is greater than 90% when using a phosphorus pentoxide to titanium dioxide mole ratio of about 1.20 to about 1.25. |
Here is a chemical reaction formula: Reactants are:m1:[O-2].[O-2].[Ti+4];m2:P(O)(O)(O)=O;m3:O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3;m4:[O-2].[O-2].[Ti+4], Reagents are:, and Products are 0:[O-]P([O-])(=O)OP(=O)([O-])[O-].[Ti+4], please give me the reaction condition of this formula. | The condition of this chemical reaction is: thermally reacting titanium dioxide and phosphoric acid at a temperature of about 400° C. to about 500° C. in a reaction mixture having a phosphorus pentoxide to titanium dioxide mole ratio of about 1.20 to about 1.25 to form a fine titanium pyrophosphate powder with greater than 90% of said fine titanium pyrophosphate powder having a particle size less than 1 micron in diameter; and |
Here is a chemical reaction formula: Reactants are:m2:ClC1=NC=C(C=N1)CCCCCCCCCC;m5_m4:C([O-])([O-])=O.[Na+].[Na+];m1:C(CCCCCCC)C1OC2=CC=C(C=C2C1)B(O)O;m3:C1=CC=CC=C1, Reagents are:m5_m4:[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m6:O, and Products are 0:C(CCCCCCCCC)C=1C=NC(=NC1)C=1C=C2CC(OC2=CC1)CCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Under nitrogen atmosphere, 0.30 g (1.09 mM) of 2-octylcoumaran-5-boronic acid, 0.26 g (1.02 mM) of 2-chloro-5-decylpyrimidine and 1.5 ml of benzene were placed in a 20 ml-round-bottomed flask. Under stirring, 0.06 g of tetrakis(triphenylphosphine) palladium (0) and 1.5 ml of a 2M-sodium carbonate aqueous solution were added to the mixture, followed by refluxing for 5.5 hours. After the reaction, the reaction mixture was poured into water and subjected to extraction with ethyl acetate. The organic layer was washed with water, dried with mirabilite and concentrated under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography and recrystallized from a mixture solvent of toluene and methanol to obtain 0.11 g of 5-(5-decylpyrimidine-2-yl)-2-octylcoumaran (Ex. Comp. No-I-17) (Yield: 22.5%). The product showed the following phase transition temperatures (°C.). ##STR96## |
Here is a chemical reaction formula: Reactants are:m5_m4:C([O-])([O-])=O.[Na+].[Na+];m2:C(C)O;m3:BrC=1C=C(C=CC1)C1=NC=C(C=N1)CCCCCCCCCC;m1:C(CCCCCCC)C1OC2=CC=C(C=C2C1)B(O)O, Reagents are:m6:C1=CC=CC=C1;m5_m4:[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, and Products are 0:C(CCCCCCCCC)C=1C=NC(=NC1)C1=CC=C(C=C1)C=1C=C2CC(OC2=CC1)CCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Under nitrogen atmosphere, 0.25 g (0.91 mM) of 2-octylcoumaran-5-boronic acid, 0.7 ml of ethanol, 0.30 g (0.80 mM) of 2-(3-bromophenyl)-5-decylpyrimidine and 1.3 ml of benzene were placed in a 20 ml-round-bottomed flask. Under stirring, 0.05 g of tetrakis(triphenylphosphine) palladium (0) and 1.3 ml of a 2M-sodium carbonate aqueous solution were added successively to the mixture, followed by refluxing for 1 hour and 40 minutes. After the reaction, the reaction mixture was left standing at room temperature to precipitate a crystal. The crystal was washed with water and dissolved in toluene. The solution was dried with mirabilite and the solvent was distilled off under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography and recrystallized from a mixture solvent of toluene and methanol and further recrystallized from acetone to obtain 0.28 g of 5-[4-(5-decylpyrimidine-2-yl)phenyl]-2-octylcoumaran (Ex. Comp. No. I-154) (Yield: 66.5%). The product showed the following phase transition temperatures (°C.). ##STR98## |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m5:OCCOC1=C(C=CC=C1)O;m1_m2_m4_m5:C(C)N(CC)CC;m1_m2_m4_m5:O1CCCC1;m3:C(C=C)(=O)Cl, Reagents are:m1_m2_m4_m5:C1=CC=CC=2SC3=CC=CC=C3NC12, and Products are 0:C(C=C)(=O)OC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 500-ml, two necked flask was equipped with magnetic stirring bar, nitrogen atmosphere and an addition funnel. The flask was charged with 25 g of 2-(2-hydroxyethoxy)phenol (0.16 mol.), 33 g of triethylamine (0.32 mol.), 250 ml of tetrahydrofuran and 1 g of phenothiazine. Next, 30 g of acryloyl chloride (0.18 mol.) was slowly added to the reaction over 1 hour via the addition funnel. The triethylamine hydrochloride salt was removed by filtration and the mother liquor was evaporated with a rotoevaporator. The remaining liquid was dissolved in chloroform and washed with NaCl(aq.), NH4OH(10%), NaCl(aq.) and dried over MgSO4. The chloroform was removed with a rotoevaporator to yield 26 g (62%) of a reddish brown liquid. The product was confirmed by IR and 13C NMR. |
Here is a chemical reaction formula: Reactants are:m1_m3:NCCOCCO;m2:C1(C2C(C(=O)O1)CCCC2)=O, Reagents are:m1_m3:C(C)O, and Products are 0:OCCOCCN1C(C2C(C1=O)CCCC2)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 500-ml, two necked flask was equipped with a magnetic stirring bar, heating mantle and condenser. The flask was charged with 51 g of 2-(aminoethoxy) ethanol (0.49 mol.) and 250 ml of ethanol. Next, 75 g of hexahydrophthalic anhydride (0.49 mol.) was slowly added to the flask. After the addition was complete the reaction was refluxed for 12 hours. The IR spectrum indicated the reaction was complete. The ethanol was removed with a rotoevaporator to yield 113 g (96%) of N-(2-hydroxyethoxyethyl)hexahydrophthalimide. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m5:OCCOCCN1C(C2C(C1=O)CCCC2)=O;m1_m2_m4_m5:C(C)N(CC)CC;m3:C(C=C)(=O)Cl, Reagents are:m1_m2_m4_m5:C1=CC=CC=2SC3=CC=CC=C3NC12;m1_m2_m4_m5:CC(=O)C, and Products are 0:C(C=C)(=O)OCCOCCN1C(C2C(C1=O)CCCC2)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A one liter, three necked flask was equipped with overhead stirrer, nitrogen atmosphere and an addition funnel. The flask was charged with 100 g of N-(2-hydroxyethoxyethyl)hexahydrophthalimide (0.41 mol.), 42 g of triethylamine (0.41 mol.), 1 g of phenothiazine and 400 ml of acetone. Next, 38 g of acryloyl chloride (0.41 mol.) was added slowly to the flask via the addition funnel over 45 minutes. The reaction was stirred for an additional 12 hours. The triethylamine hydrochloride salt was removed by filtration and the remaining mother liquor was evaporated with a rotoevaporator. The resulting red-orange liquid was dissolved in chloroform and extracted with HCl(10%), NaCl(aq.), NH4OH(10%), NaCl(aq.) and dried over MgSO4. The chloroform was removed with a rotoevaporator to yield 72 g (59%) of an orange-red liquid. The product was confirmed by IR and 13C NMR. |
Here is a chemical reaction formula: Reactants are:m2:O1C(=CC=C1)C(=O)Cl;m1_m3:CNCCO, Reagents are:m1_m3:ClCCl, and Products are 0:OCCN(C(=O)C=1OC=CC1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A one liter, three necked flask was equipped with overhead stirrer, nitrogen atmosphere and an addition funnel. The flask was charged with 115 g of 2-(methylamino)ethanol (1.53 mol.) and 500 ml of dichloromethane. The reaction flask was cooled with an ice bath. Next, 100 g of furoyl chloride (0.77 mol.) was slowly added via the addition funnel over 2.5 hours. The dichloromethane was washed with NaCl(aq.). Next, the NaCl(aq.) layer was extracted with dichloromethane and the two dichloromethane layers were combined and dried over MgSO4. The dichloromethane was removed with a rotoevaporator to yield 75 g (44%) of N-(2-hydroxyethyl)-N-methylfuranamide. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C(=C)C)(=O)OCCN=C=O;m1_m2_m3:C(C1=CC=CC=C1)O, Reagents are:m1_m2_m3:O1CCOCC1;m4:C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCC)[Sn+2]CCCC, and Products are 0:C(C(=C)C)(=O)OCCNC(=O)OCC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 77.5 g of methacryloyloxyethyl isocyanate (Karenzu MOI, available from Showa Denko K.K.) and 60 g of benzyl alcohol were dissolved in 260 g of dioxane. To the solution were then added 5 drops of di-n-butyltin dilaurate. The reaction mixture was then allowed to undergo reaction at a temperature of 65° C. for 3 hours. The dioxane and excess benzyl alcohol were then distilled off under reduced pressure. The residue was poured into water, extracted with ethyl acetate, and then dried. The solvent was then distilled off to obtain 106 g of benzyloxycarbonylaminoethyl methacrylate in the form of colorless oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(=O)(O)CCC(=O)C1=CC=C(C=C1)C(=O)C1(CCCCC1)O;m1_m2_m3:S(=O)(Cl)Cl, Reagents are:m1_m2_m3:C(C)OCC, and Products are 0:ClC(=O)CCC(=O)C1=CC=C(C=C1)C(=O)C1(CCCCC1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 250-ml round-bottomed flask fitted with a condenser was charged with 12.0 g of 1-hydroxycyclohexyl 4-(2-carboxyethyl)carbonylphenyl ketone (0.04 mole), 5.95 g (0.05 mole) of thionyl chloride (Aldrich), and 50 ml of diethyl ether. The resulting reaction mixture was stirred at 30° C. for 30 minutes, after which time the solvent was removed under reduced pressure. The residue, a white solid, was maintained at 0.01 Torr =30 minutes to remove residual solvent and excess thionyl chloride, leaving 12.1 g (94 percent) of 1-hydroxycyclohexyl 4-(2-chloroformylethyl)carbonylphenyl ketone. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2_m4:[N+](=O)([O-])C=1C=C(C=CC1)N=C=O;m1_m3_m2_m4:C12(CC3CC(CC(C1)C3)C2)CN2C(C(C(N(C3=C2C=CC=C3)C3=CC=CC=C3)=O)N)=O, Reagents are:m5:ClCCl;m1_m3_m2_m4:C(C)#N;m1_m3_m2_m4:C(C)#N, and Products are 0:C12(CC3CC(CC(C1)C3)C2)CN2C(C(C(N(C3=C2C=CC=C3)C3=CC=CC=C3)=O)NC(=O)NC3=CC(=CC=C3)[N+](=O)[O-])=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 3-nitrophenyl isocyanate (0.082 g) in dry acetonitrile (8 ml) was added to a solution of the 1-(1-Adamantylmethyl-3-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (0.2 g) in dry acetonitrile (10 ml) under a nitrogen atmosphere. The mixture was stirred at 23° for 2 h, then diluted with dichloromethane (15 ml) and washed with brine (15 ml). The organic solution was dried, concentrated in vacuo and the residue was triturated with diethyl ether to give the title compound as a white solid (0.229 g). M.p. 213°-5°. T.I.c. CH-EA (2:1), Rf0.33. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:COC1=C2N=CN(C2=NC=N1)COCCP(OCC)(OCC)=O;m1_m3_m2:N, Reagents are:m1_m3_m2:CO, and Products are 0:N1=CN=C2N(C=NC2=C1N)COCCP(OCC)([O-])=O.[NH4+], please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 11 (3.44 g, 10.0 mmol) in MeOH (40 mL) was added a saturated methanolic NH3 solution (100 mL). The solution was heated in a sealed flask at 100° C. for 30 h. The solvent was evaporated and the residue was crystallized from EtOH to give 12 (1.20 g) in 40% yield: mp 190°-193° C.; TLC Rf 0.37 (AcOEt/MeOH=1:1); UV λmax (EtOH): 260 nm (ε14 000); 1H NMR (DMSO-d6 /D2O): δ1.20-1.56 (m, 5 H, CH3 +CH2 P), 3.40-4.10 (m, 2 H, CH2OP), 4.30 (m, 2 H, CH2O), 5.60 (s, 2 H, OCH2N), 7.80, 8.12 (2 s, 2 H, HC(2) +HC(8)). Anal. (C10 H19N6O4P) C, H, N. |
Here is a chemical reaction formula: Reactants are:m1_m4:N1=CN=C2N(C=NC2=C1N)COCCP(OCC)([O-])=O.[NH4+];m2_m3:CO;m2_m3:O, Reagents are:m1_m4:CN(C)C=O, and Products are 0:N1=CN=C2N(C=NC2=C1N)COCCP(O)(O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 12 (0.32 g, 1.0 mmol) in DMF (7.0 mL) was added Me3 SiBr (1.07 g, 7.01 mmol). After the solution was stirred at 40° C. for 6 h, a mixture of MeOH and H2O(5:1, 20 mL) was added and the solvents were evaporated. The crude residue was purified by use of column chromatography (resin XAD-4, H2O) to afford 13 (0.12 g, 45%): mp 296° C. (dec.); TLC Rf 0.32 (MeOH); UV λmax (EtOH): 259 nm (ε13 700); 1H NMR(DMSO-d6 /D2O): δ1.49 (m, 2 H, CH2P), 3.80 (m, 2 H, CH2O), 5.55 (s, 2 H, OCH2 N), 7.90, 8.19 (2 s, 2 H, HC(2)+HC(8)). Anal. (C8H12N5 O4P) C, H, N. |
Here is a chemical reaction formula: Reactants are:m7_m2_m5_m6:[OH-].[Na+];m1_m4:O[C@H]1[C@@H](CCC2=CC3=C(SCC3)C=C12)NC(CC)=O, Reagents are:m7_m2_m5_m6:O;m7_m2_m5_m6:O;m7_m2_m5_m6:O;m1_m4:O1CCCC1;m3:O1CCCC1, and Products are 0:O[C@H]1[C@@H](CCC2=CC3=C(SCC3)C=C12)NCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a 500 ml three-necked flask fitted with a magnetic stirrer and a nitrogen inlet, 2.3 g (61 mmol) of AILiH4 are suspended in 75 ml of dry tetrahydrofuran. 6.2 g (24.5 mmol) of the product obtained in Step 2 dissolved in 97 ml of dry tetrahydrofuran are slowly added at room temperature. After 18 hours' stirring at room temperature, the reaction is stopped by the addition of 1.6 ml of water, 1.3 ml of 20 % NaOH in water and finally 5.8 ml of water in succession. The reaction mixture is stirred for 0.5 hour at room temperature and then filtered. The precipitate is washed copiously with tetrahydrofuran and the flitrate is concentrated in vacuo to yield 1.37 g of the expected product in the form of a meringue, Yield: 97 %. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2_m4:C(C=C)#N;m1_m3_m2_m4:CN(CCCCN)C, Reagents are:m1_m3_m2_m4:CO;m1_m3_m2_m4:CO, and Products are 0:C(#N)CCNCCCCN(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of acrylonitrile (1.17 g, 22.07 mmol) in methanol (1.0 ml) was added dropwise to a solution of N,N-dimethyl-1,4-diaminobutane 322 (2.1 g, 18.42 mmol) in methanol (1.0 ml) at 0° C., and the mixture was stirred at 0° C. for sixteen hours. Evaporation of the solvent in vacuo afforded almost pure N-(2-cyanoethyl)-N',N'-dimethyl-1,4-diaminobutane 323 as a colorless oil (2.5 g, 80% yield based on 322). 1H NMR (400 MHz, CDCl3) δ: 1.45 (4H, m, --CH2 --CH2 --CH2 --CH2 --), 2.15 (6H, s, --N(CH3)2), 2.22 (2H, t, --CH2N), 2.47 (2H, t, --CH2CH2CN), 2.60 (2H, t, --CH2CH2NH--), 2.88 (2H, t, --CH2CH2NH--), 3.37 (1H, s, --NH). |
Here is a chemical reaction formula: Reactants are:m1_m3_m2_m4:[H-].[H-].[H-].[H-].[Li+].[Al+3];m1_m3_m2_m4:C(C)(C)(C)OC(=O)N(CCCCN(C)C)CCC#N, Reagents are:m1_m3_m2_m4:CCOCC;m1_m3_m2_m4:CCOCC, and Products are 0:NCCCN(CCCCN(C)C)C(=O)OC(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of LAH (0.62 mg, 16.30 mmol) in anhydrous ether (100 ml) was added N-(tert-butoxycarbonyl)--N-(2-cyanoethyl)-N',N'-dimethyl-1,4-diaminobutane 324 (2.22 g, 8.10 mmol) in anhydrous ether (50 ml) at 0° C. The mixture was stirred at 0° C. for thirty minutes. The excess LAH was quenched with 1N NaOH at 0° C., and the resulting suspension was filtered through Celite and washed with ether. The combined ether layers were washed with brine, dried over MgSO4, and concentrated in vacuo to yield a crude product. The crude product was purified on a flash silica gel column and eluted with chloroform:methanol:isopropylamine (15:1:1) to give N-(3-aminopropyl)--N-(tert-butoxycarbonyl)-N',N'-dimethyl-1,4-diaminobutane 325 (1.30 g, 59% yield). 1H NMR (400 MHz, CDCl3) δ: 1.40 (9H, s, t-Bu), 2.15 (6H, s, --N(CH3)2), 2.22 (2H, m), 2.65 (2H, t), 3.20 (4H, m). |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:C(C)(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(=O)O)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C;m1_m3_m2:C(C(=O)Cl)(=O)Cl, Reagents are:m1_m3_m2:ClCCl, and Products are 0:C(C)(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(=O)Cl)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 3β-acetoxy-5-cholenic acid (50.0 g, 118 mmole) in dry dichloromethane (200 ml) was added dropwise oxalyl chloride (30 ml, 448 mmole). The solution was stirred at room temperature for one hour and then concentrated in vacuo to obtain 3β-acetoxy-5-cholenic acid chloride 331. 1H NMR (400 MHz, CDCl3) δ: 0.70 (3H, s, 18-CH3), 0.95 (3H, d, 21-CH3), 1.05 (3H, s, 19-CH3), 2.04 (3H, s, --OCOCH3), 4.60 (1H, m, 3α-H), 5.38 (1H, m, 6-H). Compound 331 was used in the following step without purification. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2_m4:NCCCCN;m1_m3_m2_m4:C(C=C)#N, Reagents are:m1_m3_m2_m4:CO;m1_m3_m2_m4:CO, and Products are 0:C(#N)CCNCCCCN, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1,4-diaminobutane (4.3 g, 48.8 mmole) in methanol (1.5 ml) was added a solution of acrylonitrile (3.1 g, 58.4 mmole) in methanol (1.5 ml) at 0° C., and the mixture was stirred for twelve hours. Evaporation of the solvent in vacuo afforded N-(2'-cyanoethyl)-1,4-diaminobutane as a colorless oil (5.5 g, 80% yield). 1H NMR (400 MHz, CDCl3) δ: 1.45 (4H, br, --CH2 CH2 --), 2.46 (2H, t), 2.58 (2H, t), 2.62 (2H, t), 2.84 (2H, t). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)(=O)OCCCC1=C(NC(=C1C)C=O)CC=1NC(=C(C1CC)CC)CC=1NC(=C(C1CCCOC(C)=O)C)C=O;m1_m2_m3:[Li+].[OH-], Reagents are:m1_m2_m3:CO, and Products are 0:C(=O)C1=C(C(=C(N1)CC=1NC(=C(C1CC)CC)CC=1NC(=C(C1CCCO)C)C=O)CCCO)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 7H, FIG. 7. 2,5-Bis[(3-acetoxypropyl-5-formyl-4-methylpyrrol-2-yl)methyl]-3,4-diethylpyrrole 7G (5.98 g, 0.011 mol) and LiOH (1.76 g, 0.042 mol) were added to 400 mL of 95% methanol, which had been degassed with nitrogen prior to use, add the mixture heated to reflux under a nitrogen atmosphere. The reaction became homogeneous when heated. After heating for 1.25 hours, the reaction was allowed to cool to room temperature. The product precipitated as a tan color solid as the reaction cooled. The volume of the reaction mixture was reduced to 75 mL on a rotary evaporator and the resulting slurry placed in the freezer for several hours. The product was filtered, and then purified by forming a slurry with 400 mL of methanol and 50 mL of water and heating close to boiling. The slurry was first cooled to room temperature, reduced to 1/2 volume under reduced pressure, and placed in the freezer for several hours. The product was collected by filtration and vacuum dried to yield 4.96 g of a tan powder (94%): 1H NMR (CD3OD, 300 MHz): δ0.96 (6H, t, CH2CH3), 1.49 (4H, p, CH2CH2CH2OH), 2.25 (6H, s, pyrrole-CH3), 2.32-2.43 (8H, m, CH2CH3 and CH2CH2CH2OH), 3.46 (4H, t, CH2CH2CH2OH), 3.85 (4H, s, (pyrrole)2 --CH2),9.34 (2H, s, CHO); CI MS (M+) 480; HRMS (M)+, 481.2942 (calc for C28H39N3O4, 481.2941). |
Here is a chemical reaction formula: Reactants are:m1_m3:OC1=C(C(=NC2=CC=CC=C12)C(=O)OC)C(=O)OC;m2:O.NN, Reagents are:m1_m3:C(C)O, and Products are 0:OC1=C2C(=NC=3C=CC=CC13)C(NNC2=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred suspension of dimethyl 4-hydroxyquinoline-2,3-dicarboxylate (1.00 g, 3.83 mM, prepared as described by H. Biere and W. Seelen, Liebigs Ann. Chem. 1976, 1972) in ethanol (15 mL) was added hydrazine hydrate (9.64 g, 193 mM) whereupon the solids dissolved. The resulting solution was refluxed for 3 hr during which time a thick precipitate formed. The cooled reaction mixture was filtered and the collected yellow solids were washed with ethanol and then ether. Air drying provided 0.99 g of the hydrazine salt of 2,3-dihydro-10-hydroxypyridazino[4,5-b]quinoline-1,4-dione. This material was boiled in glacial acetic acid (40 mL) and, after cooling to room temperature, the mixture was filtered. The collected solids were washed with several portions of ethyl acetate and then ether. Air drying provided the title pyridazinodione (0.72 g, 82%) as a yellow solid, mp>400° C.; Mass Spectrum (Chemical Ionization): 230 (M+H). |
Here is a chemical reaction formula: Reactants are:m4:CC(C)([O-])C.[K+];m3:C(#CC(=O)OC)C(=O)OC;m1_m2_m5:NC1=C(C(=O)OC)C=CC(=C1)Cl;m1_m2_m5:C(#CC(=O)OC)C(=O)OC, Reagents are:m1_m2_m5:C(C)(C)(C)O, and Products are 0:ClC1=CC=C2C(=C(C(=NC2=C1)C(=O)OC)C(=O)OC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred mixture of methyl 2-amino-4-chlorobenzoate (2.50 g, 13.5 mM) and dimethyl acetylenedicarboxylate (2.05 g, 14.4 mM) in t-butanol (22 mL) was refluxed for 7 hr under a nitrogen atmosphere. After adding additional dimethyl acetylenedicarboxylate (1.16 g, 8.13 mM) and refluxing another 2.5 hr, the reaction mixture was allowed to cool to room temperature and potassium t-butoxide (1.56 g, 13.9 mM) was added in one portion. A precipitate formed and the resulting mixture was refluxed for 1.5 hr. The mixture was cooled to room temperature and filtered to separate the solids, which were washed with t-butanol and ether. The solids were dissolved in water and acidified with 1N sulfuric acid to form a precipitate. The resulting mixture was extracted with methylene chloride and the combined extracts were washed with brine and water, dried (MgSO4), filtered and concentrated to give a green solid. Recrystallization of this material from methanol provided dimethyl 7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (1.15 g, 28.9%) as an off-white solid, mp 232-233° C.; MS(CI): 296 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m3:NC1=C(C(=O)O)C(=CC=C1)Cl;m2:ClC(Cl)(Cl)OC(OC(Cl)(Cl)Cl)=O, Reagents are:m1_m3:O1CCCC1, and Products are 0:ClC1=CC=CC2=C1C(OC(N2)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred warm (50° C.) solution of 2-amino-6-chlorobenzoic acid (2.00 g, 11.7 mM) in tetrahydrofuran (20 mL) was added bis(trichloromethyl)carbonate (1.20 g, 4.10 mM). A vigorous gas evolution ensued along with the formation of a precipitate. The reaction mixture was allowed to cool to room temperature and the precipitate was collected by filtration and washed with ether. Air drying gave the title compound as a tan solid (2.0 g, 87%); MS(CI): 198 (M+H). |
Here is a chemical reaction formula: Reactants are:m3:CC(C)([O-])C.[K+];m1_m2_m4:NC1=C(C(=O)OC)C(=CC=C1)Cl;m1_m2_m4:C(#CC(=O)OC)C(=O)OC, Reagents are:m1_m2_m4:C(C)(C)(C)O, and Products are 0:ClC1=C2C(=C(C(=NC2=CC=C1)C(=O)OC)C(=O)OC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of methyl 2-amino-6-chlorobenzoate (3.00 g, 16.2 mM) and dimethyl acetylenedicarboxylate (2.64 g, 18.6 mM) in t-butanol (25 mL) was refluxed under a nitrogen atmosphere for 18 hr. The reaction mixture was cooled to room temperature and potassium t-butoxide (2.09 g, 18.6 mM) was added in one portion whereupon a precipitate formed. After refluxing this mixture for 1.5 hr, it was cooled to room temperature and filtered to separate the solids. The solids were dissolved in rarer and the resulting solution acidified with 1N H2SO4 to form a precipitate. The mixture was filtered and the collected solids were washed with water and air dried to give dimethyl 5-chloro-4-hydroxyquinoline-2,3-dicarboxylate (3.84 g, 80.2%) as a tan solid. An 0.25 g portion of this material was recrystallized from ethyl acetate to provide an analytical sample (0.152 g) of the title compound as an off-white solid, mp 174°-176° C.; MS(CI): 296 (M+H). Analysis for C13H10ClNO5.0.01 H2O: Calculated: C, 52.78; H, 3.41; N, 4.73 Found: C, 52.39; H, 3.38; N, 4.67 |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5:ClC1=C2C(C(NC2=CC(=C1)Cl)=O)=O;m1_m2_m3_m5:C(C)(=O)O, Reagents are:m1_m2_m3_m5:C(C)(=O)OC(C)=O;m1_m2_m3_m5:[O-2].[O-2].[O-2].[Cr+6];m4:O;m6:[O-2].[O-2].[O-2].[Cr+6], and Products are 0:ClC1=CC(=CC2=C1C(OC(N2)=O)=O)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 4,6-dichloro-1H-indole-2,3-dione (5.00 g, 23.2 mM) in acetic acid (21 mL) and acetic anhydride (21 mL) at 80° C. was added in small portions chromium trioxide (4.12 g, 41.3 mM). The temperature of the reaction mixture was maintained between 80°-90° C. during the addition of the chromium trioxide. After the addition was complete, the reaction mixture was diluted with water (100 mL) and then filtered to separate the precipitated solids. The solids were washed thoroughly with water and then dried to obtain the title compound as a yellow solid (4.13 g, 72%); MS(CI): 232 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:[OH-].[Na+];m1_m3_m2:ClC1=CC(=CC2=C1C(OC(N2)=O)=O)Cl, Reagents are:m1_m3_m2:CO, and Products are 0:NC1=C(C(=O)OC)C(=CC(=C1)Cl)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of sodium hydroxide (0.070 g, 1.8 mM) in methanol (8.5 mL) was added 5,7-dichloro-2H-3,1-benzoxazine-2,4(1H)-dione (4.13 g, 17.8 mM). The reaction mixture was stirred at 55° C. for 2 hr, allowed to cool to room temperature and concentrated. The residue was diluted with water and the resulting mixture extracted with ethyl acetate. The combined extracts were dried (MgSO4), filtered and concentrated to leave the methyl 2-amino-4,6-dichlorobenzoate (3.61 g, 92.1%) as a brown solid; MS(CI): 220 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:NC1=C(C(=O)OC)C(=CC(=C1)Cl)Cl;m1_m2_m4:C(#CC(=O)OC)C(=O)OC;m3:CC(C)([O-])C.[K+], Reagents are:m1_m2_m4:C(C)(C)(C)O, and Products are 0:ClC1=C2C(=C(C(=NC2=CC(=C1)Cl)C(=O)OC)C(=O)OC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of methyl 2-amino-4,6-dichlorobenzoate (1.30 g, 5.91 mM) and dimethyl acetylenedicarboxylate (0.96 g, 6.78 mM) in t-butanol (14 mL) was refluxed for 18 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and potassium t-butoxide (0.76 g, 6.8 mM) was added to the stirred mixture whereupon a precipitate formed. After refluxing for 1.5 hr, the reaction mixture was cooled to room temperature and filtered to separate the precipitated solids. The solids were washed with t-butanol and then dissolved in water. The resulting solution was acidified with 1N H2SO4 and the resulting precipitate was collected, washed thoroughly with water and dried to give the title compound as a light green solid (1.15 g, 59%). An analytical sample was obtained by recrystallization of a portion from toluene to provide the title compound as a light tan solid, mp 109.5°-111° C. (d); MS(CI): 330 (M+H). |
Here is a chemical reaction formula: Reactants are:m3:CC(C)([O-])C.[K+];m1_m2_m4:NC1=C(C(=O)OC)C(=CC=C1)C;m1_m2_m4:C(#CC(=O)OC)C(=O)OC, Reagents are:m1_m2_m4:C(C)(C)(C)O, and Products are 0:OC1=C(C(=NC2=CC=CC(=C12)C)C(=O)OC)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred mixture of methyl 2-amino-6-methylbenzoate (1.50 g, 9.08 mM) and dimethyl acetylenedicarboxylate (1.40 g, 9.82 mM) in t-butanol (20 mL) was refluxed fpr 18 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and potassium t-butoxide (1.10 g, 9.82 mM) was added in one portion whereupon a precipitate formed. After refluxing this mixture for 1.5 hr, it was cooled to room temperature and filtered to separate the solids. The solids were dissolved in water and the resulting solution acidified with 1N H2SO4 to form a precipitate. The mixture was filtered and the collected solids were washed with water and dried to give the title compound (1.66 g, 66.4%) as a tan solid. An analytical sample of this material was obtained by recrystallization of a portion from ethyl acetate/hexane to give off white crystals, mp 167°-168° C.; MS(CI): 276 (M+H). |
Here is a chemical reaction formula: Reactants are:m5_m7:Cl.NO;m1_m2_m6_m3_m4_m8:ClC(C(O)O)(Cl)Cl;m1_m2_m6_m3_m4_m8:S(=O)(=O)([O-])[O-].[Na+].[Na+];m1_m2_m6_m3_m4_m8:CC=1C=C(N)C=C(C1)C;m1_m2_m6_m3_m4_m8:Cl, Reagents are:m5_m7:O;m1_m2_m6_m3_m4_m8:O;m1_m2_m6_m3_m4_m8:O, and Products are 0:CC=1C=C(C=C(C1)C)NC(C=NO)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of chloral hydrate (14.1 g, 85.24 mM) and sodium sulfate (88.2g, 7.53 eq.) in 270 mL of water was added a solution of 3,5-dimethylaniline in a solution of concentrated HCl (16 mL) and water (51 mL), whereupon an off-white precipitate formed. The mixture was stirred for 10 min prior to adding an aqueous solution of hydroxylamine hydrochloride (17.4 g, 250 mM) in water (50 mL) and then heated at reflux for 10 min during which time the solids dissolved and a tan precipitate formed. The mixture was cooled and filtered, and the collected solids were air dried to yield the title compound (15.0 g, 95%). |
Here is a chemical reaction formula: Reactants are:m2:CC=1C=C(C=C(C1)C)NC(C=NO)=O;m1_m3:OS(=O)(=O)O, Reagents are:m1_m3:O, and Products are 0:CC1=C2C(C(NC2=CC(=C1)C)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred warm (60°-70° C.) solution of concentrated H2SO4 (60 mL) and water (6 mL) was added in small portions N-(3,5-dimethylphenyl)-2-(hydroxyimino)acetamide (15.0 g, 78 mM) so that the temperature of the reaction mixture did not exceed 70° C. After the addition was completed, the reaction mixture was heated at 80° C. for 10 min and then cooled and poured onto ice. The resulting mixture was filtered and the collected solids were washed with water and dried to provide the title compound (9.93 g, 72.6%); MS(CI): 176. |
Here is a chemical reaction formula: Reactants are:m2:O;m1_m3:CC1=C2C(C(NC2=CC(=C1)C)=O)=O, Reagents are:m4:[O-2].[O-2].[O-2].[Cr+6];m1_m3:C(C)(=O)O, and Products are 0:CC1=CC(=CC2=C1C(OC(N2)=O)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred warm (60° C.) solution of 4,6-dimethyl-1H-indole-2,3-dione (2.0 g, 11.4 mM) in acetic acid (20 mL) was added in small portions chromium trioxide (6.6 g, 66 mM) while maintaining the temperature of the reaction mixture at 65°-70° C. The reaction mixture was then heated at 80° C. for one hour, cooled, poured into water (150 mL) and filtered to obtain the the title compound (0.67 g, 31%) as a light yellow solid; MS(CI): 192 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:[OH-].[Na+];m1_m3_m2:CC1=CC(=CC2=C1C(OC(N2)=O)=O)C, Reagents are:m1_m3_m2:CO, and Products are 0:NC1=C(C(=O)OC)C(=CC(=C1)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of sodium hydroxide (0.013 g, 0.33 mM) in methanol (1.7 mL) was added 5,7-dimethyl-2H-3,1-benzoxazine-2,4(1H)-dione (0.67 g, 3.5 mM). The mixture was heated to 60° C. and maintained at that temperature for 45 min during which vigorous gas evolution ensued and all solids dissolved completely. The solution was cooled and concentrated using a rotary evaporator. The residue was dissolved in ethyl acetate, and the ethyl acetate solution was washed with water, dried (Na2 SO4), filtered and concentrated to provide the title compound (0.54 g, 86%) as a tan solid; MS(CI); 180 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5:[N+](=O)([O-])C1=C(C#N)C=CC(=C1)OC;m1_m2_m3_m5:C(C)(=O)O;m1_m2_m3_m5:S(O)(O)(=O)=O, Reagents are:m1_m2_m3_m5:O;m4:O, and Products are 0:[N+](=O)([O-])C1=C(C(=O)O)C=CC(=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2-nitro-4-methoxybenzonitrile (14.0 g, 78.6 mM) in a solution of acetic acid (28 mL), sulfuric acid (28 mL) and water (28 mL) was refluxed for 11 hr, allowed to cool and diluted with water (200 mL). The resulting precipitate which formed was collected, washed with water and dried to give the title benzoic acid (14.2 g, 91.8%) as a yellow crystalline solid; MS(CI): 198 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:COC1=CC=CC(=C1C(=O)O)[N+](=O)[O-], Reagents are:m1_m2_m3:C(C)O;m1_m2_m3:[Pd], and Products are 0:NC1=C(C(=O)O)C(=CC=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 6-methoxy-2-nitrobenzoic acid (3.25 g, 16.5 mM) in ethanol (180 mL) containing 10% palladium-on-carbon catalyst (0.30g) was hydrogenated using a Parr apparatus. When hydrogen consumption ceased, the resulting mixture was filtered through diatomaceous earth and the filtrate concentrated to provide the title benzoic acid (2.76 g, 100%) as a tan solid; MS(CI): 168 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m3:NC1=C(C(=O)O)C(=CC=C1)OC;m2:ClC(Cl)(Cl)OC(OC(Cl)(Cl)Cl)=O, Reagents are:m1_m3:O1CCCC1, and Products are 0:COC1=CC=CC2=C1C(OC(N2)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred warm (50° C.) solution of 2-amino-6-methoxybenzoic acid (2.70 g, 16.2 mM) in tetrahydrofuran (25 mL) under a nitrogen atmosphere was added bis(trichloromethyl)carbonate (1.60 g, 5.38 mM), whereupon a tan precipitate formed. The reaction mixture was maintained at 50° C. for 30 min, cooled, rewarmed to 50° C. for 30 min, filtered cool and dried to provide the title compound (2.95 g, 94.6%) as an off-white solid; MS(CI): 194 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2:[OH-].[Na+];m1_m4_m2:COC1=CC=CC2=C1C(OC(N2)=O)=O;m3:O, Reagents are:m1_m4_m2:CO, and Products are 0:NC1=C(C(=O)OC)C(=CC=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of sodium hydroxide (0.06 g, 1.5 mM) in methanol (7 mL) under a nitrogen atmosphere was added 5-methoxy-2H-3,1-benzoxazine-2,4(1H)-dione (2.90 g, 15.0 mM). The reaction mixture was stirred at 65° C. for 14.5 hr, cooled to room temperature and poured into water. The resulting solution was extracted with ethyl acetate and the combined extracts were dried (Na2 SO4), filtered and concentrated to provide the title compound (2.55 g, 94%) as a tan oil; MS(CI): 182 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:NC1=C(C(=O)OC)C(=CC=C1)OC;m1_m2_m4:C(#CC(=O)OC)C(=O)OC;m3:CC(C)([O-])C.[K+], Reagents are:m1_m2_m4:C(C)(C)(C)O, and Products are 0:OC1=C(C(=NC2=CC=CC(=C12)OC)C(=O)OC)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of methyl 2-amino-6-methoxybenzoate ((1.30 g, 7.17 mM) and dimethyl acetylenedicarboxylate (1.17 g, 8.23 mM) in t-butanol (11 mL) was refluxed under a nitrogen atmosphere for 4 hr. The reaction mixture was cooled to room temperature, potassium t-butoxide (0.92 g, 8.23 mM) was added, and the resulting mixture was heated to 90° C. for 1.5 hr during which solids precipitated out of solution. The mixture was cooled to room temperature, filtered and the collected solids were dissolved in water. The resulting solution was acidified with 1N H2SO4 to form a light tan precipitate. The solids were collected, filtered, washed with water and air dried to provide the desired compound (1.35 g, 65%) as a tan solid. A 0.28 g portion of this material was recrystallized from ethyl acetate to provide an analytical sample (0.24 g) of the title compound as a white solid, mp 184°-186° C.; MS(CI): 292 (M+H). |
Here is a chemical reaction formula: Reactants are:m3:O;m1_m2_m5_m4:ClC1=C(C(=NC2=CC(=CC=C12)Cl)C(=O)OC)C(=O)OC;m1_m2_m5_m4:C(=O)[O-].[Na+], Reagents are:m1_m2_m5_m4:CN(C=O)C;m1_m2_m5_m4:C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1, and Products are 0:ClC1=CC=C2C=C(C(=NC2=C1)C(=O)OC)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred mixture of dimethyl 4,7-dichloroquinoline-2,3-dicarboxylate (5.00 g, 15.9 mM), sodium formate (1.63 g, 23.9 mM) and tetrakis(triphenylphosphine)palladium(0) (0.92 g, 0.80 mM) in anhydrous dimethylformamide (75 mL) under a nitrogen atmosphere was heated at 90°-95° C. for 7 hr. No reaction occurred so the reaction mixture was degassed and an additional quantity of tetrakis(triphenylphosphine)palladium(0) (0.92 g, 0.80 mM) was added and the reaction mixture again heated at 90°-95° C. for 6 hr. The cooled reaction mixture was poured into water and the resulting mixture extracted with ethyl acetate. The combined extracts were dried (MgSO4), filtered and concentrated to leave an gummy solid (6.0 g). Trituration of this residue with ethyl acetate and subsequent filtration separated a crystalline solid which was shown to be dimethyl 7-chloro-4-hydroxyquinoline-2,3-dicarboxylate. The filtrate was concentrated and the residue was flash chromatographed over silica gel (eluant: hexane/ethyl acetate, 3/2) to provide the title diester (1.13 g, 25.4%) as a light yellow crystalline solid; MS(CI): 280 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:NC1=C(C(=NC2=CC=CC=C12)C(=O)OC)C(=O)OC;m1_m3_m2:O.NN, Reagents are:m1_m3_m2:C(C)O, and Products are 0:NC1=C2C(=NC=3C=CC=CC13)C(NNC2=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of dimethyl 4-aminoquinoline-2,3-dicarboxylate (0.15 g, 0.58 mM) in ethanol (4 mL) was added hydrazine hydrate (1.46 g, 29.2 mM) and the resulting solution was refluxed for 3 hr. The reaction mixture was cooled to room temperature and filtered to separate the yellow precipitate (0.12 g). This material was stirred in refluxing acetic acid (4.5 mL) for 1 hr. After cooling to room temperature the reaction mixture was filtered and the collected solids washed with acetic acid and ethyl acetate. Air drying provided the title compound (0.13 g, 68%) as an orange solid, mp>400° C.; MS(CI): 229 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:NC1=C(C#N)C=CC=C1;m1_m2_m3:C(#CC(=O)OC)C(=O)OC, Reagents are:m1_m2_m3:C(C)(C)(C)O, and Products are 0:C(#N)C1=C(N/C(/C(=O)OC)=C\C(=O)OC)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-aminobenzonitrile (5.00 g, 42.3 mM) and dimethyl acetylenedicarboxylate (6.42 g, 45.2 mM) in t-butanol (70.5 mL) was refluxed under a nitrogen atmosphere for 12 hr. After cooling the reaction mixture to room temperature, a precipitate formed and was collected by filtration. The material was washed with cold methanol and air dried to give a yellow solid (4.88 g). Recrystallization of this solid from methanol provided the title compound (4.39 g, 39.9%) as yellow crystals, mp 116.5°-117.5° C.; MS(CI): 261 (M+H). Analysis for C13H12N2O4 : Calculated: C, 60.00; H, 4.65; N, 10.76 Found: C, 60.03; H, 4.67; N, 10.84 |
Here is a chemical reaction formula: Reactants are:m1_m3_m4:IC1=CC=C2C(C(NC2=C1)=O)=O;m2:O, Reagents are:m1_m3_m4:C(C)(=O)O;m1_m3_m4:C(C)(=O)OC(C)=O;m5:[O-2].[O-2].[O-2].[Cr+6], and Products are 0:IC1=CC2=C(C(OC(N2)=O)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred warm (80° C.) solution of 6-iodo-1H-indole-2,3-dione (3.0 g, 11 mM) in acetic acid (10 mL) and acetic anhydride (10 mL) was added in small portions chromium trioxide (1.83 g, 18.3 mM) while maintaining the temperature of the reaction mixture at 80°-90° C. The reaction mixture was then heated at 80° C. for 10 min, cooled and poured into water. The resulting mixture was filtered and the collected solids dried to provide the title compound as a yellow solid (2.6 g, 81.8%); MS(CI): 290 (M+H). |
Here is a chemical reaction formula: Reactants are:m3:O;m1_m4_m2:[OH-].[Na+];m1_m4_m2:IC1=CC2=C(C(OC(N2)=O)=O)C=C1, Reagents are:m1_m4_m2:CO, and Products are 0:NC1=C(C(=O)OC)C=CC(=C1)I, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of sodium hydroxide (0.048 g, 1.2 mM) in methanol (4.5 mL) was added 7-iodo-2H-3,1-benzoxazine-2,4(1H)-dione (2.6 g, 9.0 mM). The mixture was heated at 60° C. for 7 hr and the resulting solution was cooled, poured into water and extracted with ethyl acetate. The combined extracts were washed once with dilute sodium hydroxide, dried (MgSO4), filtered and concentrated to leave the title compound (2.0 g, 80%) as a brown oil which slowly crystallized; MS(CI): 278 (M+H). |
Here is a chemical reaction formula: Reactants are:m2_m4:BrC1=CC2=C(C(OC(N2)=O)=O)C=C1;m1_m3:[Na].O=C(C(=O)OCC)CC(=O)OCC, Reagents are:m2_m4:CN(C=O)C;m1_m3:CN(C=O)C, and Products are 0:BrC1=CC=C2C(=C(C(=NC2=C1)C(=O)OCC)C(=O)OCC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred mixture of diethyl oxosuccinate sodium salt (1.31 g, 6.23 mM) in dimethylformamide (DMF, 15 mL) under a nitrogen atmosphere was added a solution of 7-bromo-2H-3,1-benzoxazine-2,4(1H)-dione (1.50 g, 6.20 mM) in DMF (15 mL). The resulting reaction mixture was heated to 130° C. over 2.5 hr and then refluxed for 5 hr. After cooling to room temperature, the reaction mixture was concentrated and the residue was chromatographed over silica gel (eluant: ethyl acetate/methylene chloride; 5/95). The fractions containing the desired material were combined and concentrated. The solid residue was recrystallized from ethanol/ether to provide (0.54 g, 24%) the title compound as a tan solid, mp 233.5°-234.5° C.; MS(CI): 368, 369 (M+H). |
Here is a chemical reaction formula: Reactants are:m1:ClC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)O;m2_m3:C(CCC1=CC=CC=C1)(=O)Cl, Reagents are:m4:O;m2_m3:N1=CC=CC=C1, and Products are 0:ClC=1C=CC=2C(=C3C(=NC2C1)C(NN=C3OC(CCC3=CC=CC=C3)=O)=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 7-chloro-2,3-dihydro-10-hydroxypyridazino[4,5-b]quinoline-1,4-dione (0.60 g, 2.3 mM), as prepared in Example 2, and hydrocinnamoyl chloride (1.15 g, 6.84 mM) in pyridine (9 mL) was refluxed for 1 hr. Upon cooling to room temperature, the solution solidified. After 2 hr at room temperature, the mixture was diluted with water (60 mL) and the solids broken up with a glass rod to provide a free-flowing aqueous suspension which was stirred for 1 hr. The solids were collected, washed with water (10 mL), and resuspended in 50% aqueous methanol (60 mL). After stirring for 15 minutes, this suspension was filtered and the collected solids were washed with 50% aqueous methanol (10 mL) and then sucked dry under a stream of nitrogen to provide a tan solid. This material was dried for 2.5 days in vacuo (50 mTorr) at 100° C. and then was recrystallized from dimethylsulfoxide/methanol. The title compound was obtained (0.40 g, 44%), after drying 24 hr in vacuo (50 mTorr) at 100° C., as an off-white powder, mp>300° C. |
Here is a chemical reaction formula: Reactants are:m3:O;m2:ClC1=CC=CC=2C(OC(NC21)=O)=O;m1_m4:[Na].O=C(C(=O)OCC)CC(=O)OCC, Reagents are:m1_m4:CN(C=O)C, and Products are 0:ClC=1C=CC=C2C(=C(C(=NC12)C(=O)OCC)C(=O)OCC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred mixture of diethyl oxosuccinate sodium salt (2.31 g, 11.0 mM) in dimethylformamide (20 mL) under a nitrogen atmosphere was added 8-chloro-2H-3,1-benzoxazine-2,4(1H)-dione (2.17 g, 11.0 mM). The resulting mixture was heated slowly to 130° C. and maintained at this temperature for 2.5 hr. After cooling, the reaction mixture was poured into water and the resulting mixture was then extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried (MgSO4), filtered and concentrated to obtain an oily solid (1.55 g). This material was chromatographed (eluant: CH2C12 /CH3OH; 98/2) over silica gel to provide the title compound as an oil which slowly crystallized to a tan solid (0.700 g, 19.7%). A 0.150 g portion of this material was recrystallized from toluene/hexane to provide an analytical sample (0.050 g) of the title compound as a tan solid, mp 98°-99° C.; MS(CI): 324 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:[OH-].[Na+];m1_m3_m2:IC1=CC=CC2=C1C(OC(N2)=O)=O, Reagents are:m4:[OH-].[Na+];m1_m3_m2:CO, and Products are 0:NC1=C(C(=O)OC)C(=CC=C1)I, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of sodium hydroxide (0.35 g, 8.8 mM) in methanol (31 mL) was added 5-iodo-2H-3,1-benzoxazine-2,4(1H)-dione (18.5 g, 64.0 mM). The mixture was heated at 60° C. for 1.5 hr. An additional quantitiy of sodium hydroxide (0.10 g, 2.5 mM) was added to the reaction mixture and stirring at 60° C. was continued for an additonal 1 hr. After cooling to room temperature, the reaction mixture was concentrated and the residue was taken up in ethyl acetate. The ethyl acetate was washed successively with water, brine, dilute aqueous sodium hydroxide, and water. After drying over MgSO4, the ethyl acetate was filtered and concentrated to leave (13.9 g, 78.4%) of the title ester as a brown oil; MS(CI): 278 (M+H). |
Here is a chemical reaction formula: Reactants are:m4:O;m2:[H-].[Na+];m3:IC;m1_m5:C(C)(C)(C)OC(=O)NC1=C(C(=O)O)C(=C(C(=C1)Cl)OC)Cl, Reagents are:m1_m5:CN(C=O)C, and Products are 0:C(C)(C)(C)OC(=O)NC1=C(C(=O)OC)C(=C(C(=C1)Cl)OC)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (ice bath) stirred solution of 2-(tert-butoxycarbonylamino)-4,6-dichloro-5-methoxybenzoic acid (2.0 g, 5.9 mM) in 20 mL of dry dimethylformamide under a nitrogen atmosphere was added sodium hydride (0.24 g, 5.9 mM); a precipitate formed which slowly redissolved on stirring. To the resulting stirred solution was added iodomethane (8.4 g, 59 mM). After stirring at room temperature for 1.5 hr, the reaction mixture was poured into water and the resulting mixture extracted with ether. The combined ether extracts were washed with brine, dried (MgSO4), filtered and concentrated to leave the title compound as a yellow oil (2.0 g, 96%); MS(CI): 350 (M+H). |
Here is a chemical reaction formula: Reactants are:m2_m6:C(C)(C)(C)[Li];m4:O;m1_m5:C(C)(C)(C)OC(=O)NC1=CC(=CC(=C1)C(F)(F)F)Cl;m1_m5:O1CCCC1;m3:C(=O)=O, Reagents are:m2_m6:CCCCC, and Products are 0:C(C)(C)(C)OC(=O)C1=C(C(=O)O)C(=CC(=C1)C(F)(F)F)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-100° C.) stirred solution of N-(tert-butoxycarbonyl)-3-chloro-5-trifluoromethylaniline 93.4 g, 11.5 mM) in dry tetrahydrofuran (30 mL) under a nitrogen atmosphere was added dropwise t-butyllithium (14.2 mL of 1.7 M solution, 24.2 mM) in pentane. The temperature of the reaction mixture was maintained at -103° to -98° C. during the addition and for 3.25 hr after the addition was completed. Crushed Dry Ice was then added to the cold reaction mixture which, after being allowed to warm to -75° C., was poured into water. The resulting mixture was extracted with ethyl acetate and the combined extracts were dried (MgSO4), filtered and concentrated to leave (3.2 g, 82%) the title compound as a solid white foam. |
Here is a chemical reaction formula: Reactants are:m3:O;m1_m4_m2:NC1=C(C(=O)O)C(=CC(=C1)Cl)C(F)(F)F;m1_m4_m2:ClC(Cl)(Cl)OC(OC(Cl)(Cl)Cl)=O, Reagents are:m1_m4_m2:O1CCCC1, and Products are 0:ClC1=CC(=CC2=C1C(OC(N2)=O)=O)C(F)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 2-amino-4-chloro-6-trifluoromethylbenzoic acid (0.53 g, 2.2 mM) in dry tetrahydrofuran (6 mL) under a nitrogen atmosphere was added bis(trichloromethyl)carbonate (0.218 g, 0.734 mM). The resulting solution was stirred at room temperature for 2 hr, poured into water and the resulting mixture extracted with ethyl acetate. The combined extracts were dried (MgSO4), filtered and concentrated to leave the title compound as a tan solid; MS(CI): 266 (M+H). |
Here is a chemical reaction formula: Reactants are:m3:C(C)OCC;m1_m4_m2:[OH-].[Na+];m1_m4_m2:ClC1=CC(=CC2=C1C(OC(N2)=O)=O)C(F)(F)F, Reagents are:m1_m4_m2:CO, and Products are 0:NC1=C(C(=O)OC)C(=CC(=C1)C(F)(F)F)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of sodium hydroxide (0.012 g, 0.31 mM) in anhydrous methanol (1.5 mL) under a nitrogen atmosphere was added 5-chloro-7-trifluoromethyl-2H-3,1-benzoxazine-2,4(1H)-dione (0.60 g, 2.3 mM). The resulting mixture was warmed to 60° C. for 0.5 hr, allowed to cool to room temperature and poured into diethyl ether. The ether was washed with water, dried (MgSO4), filtered and concentrated to leave (0.50 g, 88%) the title compound as a yellow oil; MS(CI): 254 (M+H). |
Here is a chemical reaction formula: Reactants are:m3:Cl;m2:Cl;m1:NC1=C(C(=O)O)C=CC(=C1)F;m4:C([O-])(O)=O.[Na+], Reagents are:m5:CO;m6:O, and Products are 0:NC1=C(C(=O)OC)C=CC(=C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred solution of 2-amino-4-fluorobenzoic acid (4.86 g, 31.3 mM) in anhydrous methanol (100 mL) was saturated with anhydrous hydrogen chloride and then refluxed for 4 days. During the reflux period, the reaction mixture was periodically resaturated with hydrogen chloride. After the reflux period, the reaction mixture was cooled and concentrated to leave a white solid. This material was dissolved in water and the resulting solution neutralized with aqueous sodium bicarbonate and extracted with diethyl ether. The combined extracts were dried (MgSO4), filtered and concentrated to leave (4.08 g, 80.6%) of the title compound as an off white solid, mp 66°-67° C.; MS(CI): 170 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:OC1=C(C(=NC2=CC=C(C=C12)[N+](=O)[O-])C(=O)OCC)C(=O)OCC;m1_m4_m2_m3:C(C)(=O)O, Reagents are:m1_m4_m2_m3:C(C)O;m1_m4_m2_m3:[Fe], and Products are 0:NC=1C=C2C(=C(C(=NC2=CC1)C(=O)OCC)C(=O)OCC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred mixture of diethyl 4-hydroxy-6-nitroquinoline-2,3-dicarboxylate (4.4 g, 13 mM), powdered iron (6.6 g, 118 mM) and glacial acetic acid (18.5 g, 307 mM) in ethanol (80 mL) was refluxed for 20 hr under a nitrogen atmosphere. The reaction mixture was cooled and filtered and the filtrate was concentrated. The dark residue was chromatographed (eluant: methylene chloride/methanol; 98/2) over silical gel to provide (3.01 g, 75.3%) the title compound as light orange crystals, mp 219°-221° C.; MS(CI): 305 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m2:N(N)C(=O)C1=NC2=CC(=CC(=C2C(=C1C(=O)NN)O)Br)CC, Reagents are:m1_m2:C(C)(=O)O, and Products are 0:BrC=1C=2C(=C3C(=NC2C=C(C1)CC)C(NNC3=O)=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred mixture of 2,3-bishydrazinocarbonyl-5-bromo-7-ethyl-4-hydroxyquinoline (0.40 g, 1.1 mM) in glacial acetic acid (12 mL) was heated at 81° C. for 1.5 hr. After cooling to room temperature, the reaction mixture was filtered and the collected solids washed with acetic acid and air dried to provide the title compound (0.25 g, 70%) as a light brown solid, mp>400° C.; MS(CI): 336 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m3_m2_m4:CC1=CC(=C(N)C=C1)[N+](=O)[O-];m1_m3_m2_m4:ClCl, Reagents are:m1_m3_m2_m4:C(Cl)(Cl)Cl;m1_m3_m2_m4:C(Cl)(Cl)Cl, and Products are 0:ClC1=C(N)C(=CC(=C1)C)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 4-methyl-2-nitroaniline (19.69 g, 129.4 mM) in chloroform (200 mL) under a nitrogen atmosphere was added dropwise a solution of chlorine (10.15 g, 285.9 mM) in chloroform (100 mL) while maintaining the reaction mixture temperature below 30° C. The reaction mixture was stirred for 3 days and then washed with aqueous sodium bicarbonate. The organic phase was then concentrated and the residue chromatographed (eluant: hexane/diethyl ether; 9/1) over silica gel to provide (6.03 g, 25%) the title compound as an orange crystalline solid, mp 68.5°-69.5° C.; MS(CI): 187 (M+H). |
Here is a chemical reaction formula: Reactants are:m3_m5:N(=O)[O-].[Na+];m1_m2_m4:ClC1=C(N)C(=CC(=C1)C)[N+](=O)[O-];m1_m2_m4:S(O)(O)(=O)=O, Reagents are:m3_m5:O;m1_m2_m4:C(C)O, and Products are 0:ClC=1C=C(C=C(C1)[N+](=O)[O-])C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred mixture of 2-chloro-4-methyl-6-nitroaniline (7.39 g, 39.7 mM) and concentrated sulfuric acid (6.2 mL) in absolute ethanol (50 mL) at 0°-5° C. was slowly added a solution of sodium nitrite (6.85 g, 99.3 mM) in water (6 mL). The temperature of the reaction mixture was not allowed to exceed 5° C. during the addition. After the addition was completed, the reaction mixture was stirred at room temperature for 0.5 hr and then at reflux until the evolution of gas from the reaction mixture ceased. The reaction mixture was allowed to cool and was concentrated. The residue was slurried with ether and then filtered to remove the solids. The filtrate was concentrated and the residue chromatographed (eluant: diethyl ether/hexane; 1/9) to provide (6.25 g, 92%) the title compound as a yellow crystalline solid, mp 60.5-61° C.; MS(CI): 172 (M+H). |
Here is a chemical reaction formula: Reactants are:m2:[OH-].OCC[N+](C)(C)C;m3:C1(=CC=CC=C1)C;m4:CO;m1_m5:ClC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)O, Reagents are:m1_m5:O, and Products are 0:OCC[N+](C)(C)C.ClC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred suspension of 7-chloro-2,3-dihydro-10-hydroxypyridazino[4,5-b]quinoline-1,4-dione (1.00 g, 3.8 mM) in water (40 mL) was added choline hydroxide (0.86 mL, 3.8 mM, 50 weight per cent, aqueous solution). Toluene (250 mL) was added to the resulting solution and the mixture was concentrated using a rotary evaporator. The residue was diluted with toluene (250 mL) and the resulting mixture concentrated again to provide a yellow residue. This residue was stirred for 60 hr with methanol (25 mL) and the resulting suspension was filtered to separate the solids which were washed with methanol (3 mL) and then dried under a stream of nitrogen for 1 hr. Further drying of the solids in vacuo at 100° C. for 20 hr provided (0.76 g, 55%) of the title compound as a yellow powder, mp 267°-269° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)OC(=O)CCNC1=C2C(=NC=3C=C(C=CC13)Cl)C(NNC2=O)=O;m1_m2:Cl, Reagents are:, and Products are 0:C(=O)(O)CCNC1=C2C(=NC=3C=C(C=CC13)Cl)C(NNC2=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 10-(2-ethoxycarbonylethylamino)-7-chloro-2,3-dihydropyridazino[4,5-b]quinoline-1,4-dione (0.08 g, 0.22 mM) and 1N hydrochloric acid was refluxed for 1 hr and then cooled to room temperature and filtered. The collected orange solid was washed with water and air dried to provide (0.07 g, 97%) the title compound as an orange powder, mp 356°-359° C.; MS(CI): 335 (M+H). Analysis for C14H11ClN4O4.0.3 H2O: Calculated: C, 49.4; H, 3.44; N, 16.47 Found: C, 49.3; H, 3.23; N, 16.25 |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:Cl.ClC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)NN;m1_m2_m3:Cl.C(C)OC(CCN)=O, Reagents are:m1_m2_m3:N1=CC=CC=C1;m4:O, and Products are 0:C(C)OC(=O)CCNC1=C2C(=NC=3C=C(C=CC13)Cl)C(NNC2=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 7-chloro-2,3-dihydro-10-hydrazinopyridazino[4,5-b]quinoline-1,4-dione hydrochloride (1.0 g, 2.9 mM, as prepared in Example 44) and beta alanine ethyl ester hydrochloride (49.0 g, 320 mM) in pyridine (52 mL) was refluxed for 23 hr. After cooling, the vigorously stirred reaction mixture was diluted slowly with water (100mL) and then filtered to separate a fine red solid. The collected solids were washed with water and chromatographed (eluant: methanol/methylene chloride; 5/95) over silica gel to provide the title ester (0.13 g, 13%) as a red powder, mp 258°-260° C.; MS(CI): 363 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m3:BrC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)O;m2:[OH-].OCC[N+](C)(C)C, Reagents are:m1_m3:CO, and Products are 0:OCC[N+](C)(C)C.BrC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 7-bromo-2,3-dihydro-10-hydroxypyridazino[4,5-b]quinoline-1,4-dione (0.600g, 1.95 mM) in methanol (20 mL) was added choline hydroxide (0.24 g, 1.98 mM, 45% solution in methanol). The resulting solution was concentrated and the solid yellow residue was recrystallized from ethanol to provide (0.62 g, 78%) the title compound as yellow crystals, mp 227.5°-228.5° C. |
Here is a chemical reaction formula: Reactants are:m1_m3:C(=O)(OC(C)(C)C)N[C@@H](C(C)C)C(=O)N;m2:COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC, Reagents are:m1_m3:C1CCOC1, and Products are 0:C(=O)(OC(C)(C)C)N[C@@H](C(C)C)C(N)=S, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Boc-valineamide (0.5 g) was stirred in dry THF at room temperature under argon. Lawesson's reagent (1.56 g, 0.6 eq) was added and the mixture was stirred overnight. The solvent was evaporated and the residue chromatographed (silica, 2.5% methanol/dichloromethane) to give the title compound as a white solid (0.373 g, 70%). NMR(CDCl3) δ 8.59 (1H, br s), 8.09 (1H, br s), 5.41 (1H, d (br)), 4.20 (1H, dd), 1.99 (1H, m), 1.39 (9H, s), 0.90 (6H, m). |
Here is a chemical reaction formula: Reactants are:m5_m7:C(C1=CC=CC=C1)OCC=1N=C(NC1)C(C(C)C)=O;m4:CN(C)P(=O)(N(C)C)N(C)C;m6:C(=O)([O-])[O-].[K+].[K+];m3:C(C)(=O)OC(C)(C)C;m1_m8:C(C)(C)NC(C)C;m2:[Li]CCCC, Reagents are:m5_m7:C1CCOC1;m1_m8:C1CCOC1, and Products are 0:C(C1=CC=CC=C1)OCN1C(=NC=C1)C(CC(=O)OC(C)(C)C)(C(C)C)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Diisopropylamine (83 μL, 0.59 mmol) and THF (1.5 mL) were cooled to -40° C. and n-BuLi (188 μL, 0.47 mmol, 2.5M in hexane) was added. The reaction mixture was warmed to -10° C. and stirred for 15 m, recooled to -70° C. and t-butyl acetate (63 μL, 0.47 mmol) was added. The reaction was stirred for 5 m, and HMPA (254 μL, 1.41 mmol) was added. The reaction was stirred at -70° C. for 5 m and 1-(benzyloxymethylimidazol-2-yl)-2-methyl-propan-1-one (100 mg, 0.39 mmol) in THF (1.5 mL) was added dropwise. The mixture was stirred at -70° C. for 30 m, -40° C. for 30 m, -10° C. for 30 m, warmed to 23° C., poured into 10% aqueous K2CO3 and extracted with EtOAc. The combined organic extracts were washed with brine, dried (K2CO3), concentrated and flash chromatographed (silica gel, step gradient, 0-20% EtOAc/hexanes) to afford the title compound (131 mg, 90%). 1H NMR(CDCl3, 400 MHz) δ 7.25 (m, 5H), 6.96 (s, 1H), 6.91 (s, 1H), 5.69 (d, 1H, J=10 Hz), 5.65 (d, 1H, J=10 Hz), 4.53 (d, 1H, J=11 Hz), 4.48 (d, 1H, J=11 Hz), 3.23 (d, 1H, J=6 Hz), 2.57 (d, 1H, J=6 Hz), 2.14 (m, 1H), 1.39 (s, 9H); 0.97 (d, 3H, J=7 Hz), 0.75 (d, 3H, J=7 Hz); MS(ES) m/e 375 [M+H]+. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(C)(C)N1C(C(=CC2=CC=CC=C12)C(=O)OCC)=O;m1_m2_m3_m4:[OH-].[Na+];m1_m2_m3_m4:C(C)O, Reagents are:m1_m2_m3_m4:O, and Products are 0:C(C)(C)N1C(C(=CC2=CC=CC=C12)C(=O)O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 1.55 g of ethyl 1-isopropyl-2(1H)-quinolone-3-carboxylate and 0.28 g of sodium hydroxide in a solvent mixture of 10 ml of ethanol and 2 ml of water was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and after addition of dil. hydrochloric acid, the precipitated solid was collected by filtration, washed with water and dried to give 1.22 g of 1-isopropyl-2(1H)-quinolone-3-carboxylic acid. m.p. 168°-169° C. (ethyl acetate) |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:C(C)(C)NC1=C(CO)C=CC=C1;m1_m3_m2:ClC=1C(C(=C(C(C1Cl)=O)C#N)C#N)=O, Reagents are:m1_m3_m2:O1CCOCC1, and Products are 0:C(C)(C)NC1=C(C=O)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 9.6 g of 2-isopropylaminobenzyl alcohol in 200 ml of dioxane was added 13.2 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in several portions, followed by stirring for an hour. The solvent was evaporated, the reaction solution was concentrated, and methylene chloride was added thereto, followed by filtration. The filtrate was concentrated, and the resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to give 7.6 g of 2-isopropylaminobenzaldehyde. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(C)(C)NC1=C(C=O)C=CC=C1;m1_m2_m3_m4:C(CC(=O)OCC)(=O)OCC;m1_m2_m3_m4:C([O-])(O)=O.[Na+], Reagents are:m1_m2_m3_m4:C(C)(=O)OC(C)=O, and Products are 0:C(C)(C)N1C(C(=CC2=CC=CC=C12)C(=O)OCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 7.5 g of 2-isopropylaminobenzaldehyde, 11.0 g of diethyl malonate and 11.6 g of sodium bicarbonate in 800 ml of acetic anhydride was stirred under heating at 100° C. for 15 hours. After evaporation of the solvent under reduced pressure, water was added, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give 7.3 g of ethyl 1-isopropyl-2(1H)-quinolone-3-carboxylate. |
Here is a chemical reaction formula: Reactants are:m4:Cl;m1_m2_m5_m3:C(C)OC(=O)C=1C(NC2=CC=CC=C2C1C1=CC2=C(C=C1)OCO2)=O;m1_m2_m5_m3:CO;m1_m2_m5_m3:[OH-].[K+], Reagents are:m1_m2_m5_m3:O, and Products are 0:C1OC=2C=C(C=CC2O1)C1=C(C(NC2=CC=CC=C12)=O)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1,2-dihydro-4-(3,4-methylenedioxyphenyl)-2-oxo-3-quinoline carboxylic acid ethyl ester (40 g, 118.6 mmol), methanol (200 ml), water (300 ml) and potassium hydroxide (33.3 g, 593.5 mmol) was refluxed with heat for 40 hours. To the reaction mixture was added 110 ml of 6N-HCl to acidify the mixture to obtain a precipitated crystal by filtration. The crystal obtained was washed with diethylether to give 35 g (yield: 95.4%) of the title compound. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m3:C(C)OC(=O)C=1C(NC2=CC=CC=C2C1C1=CC=CC=C1)=O;m1_m2_m5_m3:C(C)O;m1_m2_m5_m3:[OH-].[K+];m4:Cl, Reagents are:m1_m2_m5_m3:O, and Products are 0:C1(=CC=CC=C1)C1=C(C(NC2=CC=CC=C12)=O)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1,2-dihydro-4-phenyl-2-oxo-3-quinoline carboxylic acid ethyl ester (5 g, 17 mmol), ethanol (20 ml), water (40 ml) and potassium hydroxide (5 g, mmol) was refluxed with heat for 1.5 hours. To the reaction mixture was added 60 ml of 2N-HCl to acidify the mixture to obtain a precipitated crystal by filtration. The crystal obtained was recrystallized from ethanol to give 4.2 g (yield: 92.9%) of the title compound. |
Here is a chemical reaction formula: Reactants are:m2:CN(CCN)C;m1:ClC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)F, Reagents are:, and Products are 0:Cl.Cl.CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 6-chloro-3-fluoro-7H-indeno[2,1-c]quinoline-7-on (860 mg, 3.0 mmol) in pyrydine (10 ml) was added N,N-dimethylethylenediamine (800 mg, 9.0 mmol), and the mixture was stirred with heat at 90° C. for 12 hours. The reaction mixture was distilled to dryness. To the residue was added water and chloroform for extraction. The chloroform layer was dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (eluent; chloroform:ethanol=10:1(v/v)). The purified material was dissolved in 20 ml of tetrahydrofuran. To the the solution was added 4N-hydrochloride/dioxane (2 ml) and the mixture was concentrated under reduced pressure. The residue obtained was crystallized from diethylether to give 420 mg (yield 34.3%) of title compound. The physicochemical properties thereof are shown in table 1. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)OC;m1_m3_m2:Br, Reagents are:m1_m3_m2:C(C)(=O)O, and Products are 0:CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 6-(((dimethylamino)ethyl)amino)-3-methoxy-7H-indeno[2,1-c]quinoline-7-on obtained in example 1 (3 g, 8.6 mmol) in acetic acid (40 ml) was added 47% aqueous hydrobromic acid (40 ml), and the mixture was refluxed with heat for 60 hours. The reaction mixture was distilled to dryness. To the residue was added water and the solution was adjusted to a pH of about 8 with aqueous ammonia, and subsequently extracted with chloroform. The chloroform layer was dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (eluent; chloroform:methanol:water=8:3:1(v/v/v)) and crystallized from cyclohexane to give 2.1 g (yield: 73.0%) of title compound. The physicochemical properties thereof are shown in table 1. |
Here is a chemical reaction formula: Reactants are:m1_m4_m5_m2:CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)O;m1_m4_m5_m2:C(C(C)(C)C)(=O)Cl;m3:O, Reagents are:m1_m4_m5_m2:ClCCl;m1_m4_m5_m2:CN(C1=CC=NC=C1)C, and Products are 0:CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)OC(C(C)(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 6-(((dimethylamino)ethyl)amino)-3-hydroxy-7H-indeno[2,1-c]quinoline-7-on obtained in example 3 (100 mg, 0.3 mmol) in dichloromethane (10 ml) was added 4-dimethylaminopyridine (100 mg, 0.8 mmol) and pivaloyl chloride (37 μl, 0.3 mmol), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added water to wash the organic layer, which was dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (eluent; chloroform:ethanol=10:1(v/v)) and crystallized from hexane to give 105 mg (yield: 80.0%) of title compound. The physicochemical properties thereof are shown in table 1. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(#N)C=1C(=NC(=NC1)SC)O;m1_m2:P(=O)(Cl)(Cl)Cl, Reagents are:, and Products are 0:ClC1=NC(=NC=C1C#N)SC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 5-cyano-4-hydroxy-2-methylsulfanylpyrimidine (48.33 g) from Example 1 and phosphorus oxychloride (150 mL) was heated at reflux for 3 hours. The reaction mixture was allowed to cool to room temperature, filtered, and the filtrate was concentrated to dryness under vacuum. The residue was partitioned between methylene chloride and ice water. The organic layer was separated, washed with water, dried over magnesium sulfate, filtered, and evaporated under reduced pressure. The residue was heated to reflux in hexane (750 mL) with stirring. The hot hexane solution was decanted from the insoluble material and allowed to cool to room temperature to afford 32 g of the title compound 4-chloro-5-cyano-2-methylsulfanyl-pyrimidine. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2:C(#N)C=1C(=NC(=NC1)NN)NC;m1_m4_m2:Cl;m3_m5:N(=O)[O-].[Na+], Reagents are:m1_m4_m2:O;m3_m5:O, and Products are 0:N(=[N+]=[N-])C1=NC=C(C(=N1)NC)C#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (5° C.) solution of 5-cyano-2-hydrazino-4-methylamino-pyrimidine (21.7 g) from Example 4 in a mixture of water (260 mL) and concentrated HCl (26.5 mL) was added dropwise a solution of NaNO2 (10.03 g) in water (25 mL) with overhead mechanical stirring. A white precipitate formed and after the addition was completed, the reaction was stirred for an additional 20 minutes at 5° C. The insoluble product was filtered and washed with cold water to give 22.4 g of the title compound after drying at 23° C. under high vacuum overnight. Crystallization from ethanol provided an analytically pure sample of 2-azido-5-cyano-4-methylamino-pyrimidine; mp 225°-230° C. |
Here is a chemical reaction formula: Reactants are:m1_m3:N(=[N+]=[N-])C1=NC=C(C(=N1)NC)C#N;m1_m3:C(=O)O;m2:[H][H], Reagents are:m5:[Ni];m4:[Ni], and Products are 0:NC1=NC=C(C(=N1)NC)C=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 2-azido-5-cyano-4-methylaminopyrimidine (22.24 g) from Example 5 in 400 mL of 50% aqueous formic acid was added Raney Nickel catalyst (5 g). The reaction mixture was shaken under an atmosphere of hydrogen (40.1 psi) in a Parr hydrogenation apparatus. There was a vigorous evolution of gas as the mixture was shaken at room temperature. After 30 minutes the apparatus was vented, additional Raney Nickel (5 g) was added, the apparatus recharged with hydrogen, and the mixture shaken overnight. The catalyst was removed by filtration and the filtrate was evaporated under high vacuum. The residue was suspended in water and filtered. The insoluble material was collected and dissolved in 450 mL of boiling water. The aqueous solution was filtered and the pH of the filtrate was adjusted to 7 with 1N sodium hydroxide. The precipitated product was collected by filtration and recrystallized from ethanol to give 5.0 g of 2-amino-4-methylamino-5-pyrimidinecarboxaldehyde. |
Here is a chemical reaction formula: Reactants are:m3_m4:NC1=NC=C(C(=N1)N)C=O;m3_m4:ClC1=C(C(=CC=C1)Cl)CC#N;m1_m2_m5:C(C)OCC[O-].[Na+];m1_m2_m5:[Na], Reagents are:m1_m2_m5:C(C)OCCO, and Products are 0:NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: (Prepared by the method of U.S. Pat. No. 3,534,039). To a solution of sodium 2-ethoxyethoxide prepared from 0.14 g of sodium and 60 mL of 2-ethoxyethanol was added 2.07 g of 2,4-diamino-5-pyrimidinecarboxaldehyde, and 2.79 g of 2,6-dichlorophenylacetonitrile. The mixture was heated at reflux for 4 hours, allowed to cool to room temperature, and the precipitated product was filtered and washed with diethyl ether to give 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]-pyrimidine; mp 325°-332° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:CC1=C(C=CC=C1)C1=CC2=C(N=C(N=C2)N)N(C1=N)C;m1_m2:Cl;m3:O, Reagents are:, and Products are 0:NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2)C)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 6-(2-methylphenyl)-7-imino-8-methyl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamine (0.30 g) from Example 8 and concentrated HCl (0.6 mL) was added water (11 mL). The reaction mixture was refluxed for 20 hours, then allowed to cool to room temperature. The white precipitate from the reaction mixture was filtered and washed with water. The product was dried in vacuo to give 0.21 g of 2-amino-6-(2-methylphenyl)-8-methyl-pyrido[2,3-d]pyrimidin-7(8H)-one; mp 239°-241° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)C;m1_m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC(C)=O)N(C1=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 64.2 mg (0.20 mmol) of 2-amino-6-(2,6-dichlorophenyl)-8-methyl-pyrido[2,3-d]pyrimidin-7(8H)-one (from Example 12) and 1 mL of acetic anhydride was heated to reflux. The resulting solution was maintained at reflux for 20 minutes and concentrated at atmospheric pressure to about 0.25 mL volume. The solution was cooled to 25° C. and diluted with diethyl ether (1 mL). The separated crystals were filtered and washed with diethyl ether to provide N-[6-(2,6-dichlorophenyl)-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl]acetamide, wt 44.0 mg; mp 258°-260° C. |