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Here is a chemical reaction formula: Reactants are:m1_m2_m3:NC1=NC=CC=C1OCC1=CC=CC=C1;m1_m2_m3:ClC(C(C)=O)CC=C, Reagents are:m1_m2_m3:C(C)O, and Products are 0:C(C1=CC=CC=C1)OC=1C=2N(C=CC1)C(=C(N2)C)CC=C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-amino-3-benzyloxypyridine (3 g) and 3-chloro-5-hexen-2-one (2.981 g) in ethanol (15 ml) was stirred and refluxed for 45 hours and then evaporated in vacuo. To the residue was added an aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The oily residue was purified by column chromatography on silica gel (50 g) using methylene chloride and then chloroform as eluents. The eluate with chloroform was evaporated in vacuo and the residual solid was recrystallized from diisopropyl ether to give 8-benzyloxy-3-allyl-2-methylimidazo[1,2-a]pyridine (0.31 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:NC1=NC=CC=C1OCC1=CC=CC=C1;m1_m2_m3:S(=O)(=O)(C1=CC=C(C)C=C1)OC(C(C)=O)CC#C, Reagents are:m1_m2_m3:C(C)O, and Products are 0:C(C1=CC=CC=C1)OC=1C=2N(C=CC1)C(=C(N2)C)CC#C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-amino-3-benzyloxypyridine (2 g) and 3-tosyloxy-5-hexyn-2-one (2.66 g) in ethanol (15 ml) was stirred and refluxed for 24 hours and then evaporated in vacuo. To the residue was added an aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The oily residue was purified by column chromatography on silica gel (50 g) using chloroform as an eluent to give a solid, which was recrystallized from a mixture of methylene chloride and diethyl ether to give 8-benzyloxy-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (0.855 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:NC1=NC=CC=C1NCC1=C(C=CC=C1)C;m1_m2_m3:S(=O)(=O)(C)OC(C(C)=O)CC#C, Reagents are:m1_m2_m3:C(C)O, and Products are 0:CC1=C(CNC=2C=3N(C=CC2)C(=C(N3)C)CC#C)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-amino-3-(2-methylbenzylamino)pyridine (2 g) and 3-mesyloxy-5-hexyn-2-one (1.78 g) in ethanol (40 ml) was refluxed for 31.5 hours and then evaporated in vacuo. The residue was treated with aqueous sodium bicarbonate solution and extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (40 g) with a mixtutre of methylene chloride and ethyl acetate (50:1 to 10:1) as an eluent to give 8-(2-methylbenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (0.82 g). |
Here is a chemical reaction formula: Reactants are:m4:C([O-])(O)=O.[Na+];m1_m2_m3_m5:C([O-])(O)=O.[Na+];m1_m2_m3_m5:NC1=NC=CN=C1OCC1=C(C=CC=C1)C;m1_m2_m3_m5:S(=O)(=O)(C)OC(C(C)=O)CC#C, Reagents are:m1_m2_m3_m5:C(C)O, and Products are 0:CC1=C(COC=2C=3N(C=CN2)C(=C(N3)C)CC#C)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Sodium bicarbonate (2.73 g) was added to a solution of 2-amino-3-(2-methylbenzyloxy)pyrazine (3.5 g) and 3-mesyloxy-5-hexyn-2-one (6.18 g) in ethanol (35 ml) and the mixture was refluxed for 12 hours. The mixture was poured into an aqueous solution of sodium bicarbonate and extracted with chloroform. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (200 g) with a mixture of chloroform and methanol (50:1) as an eluent to give 8-(2-methylbenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyrazine (0.182 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)CC#C)C=CC=C1;m1_m2_m3:[OH-].[Na+], Reagents are:m1_m2_m3:CO, and Products are 0:CC1=C(COC=2C=3N(C=CC2)C(=C(N3)C)C=C=C)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 8-(2-methylbenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (0.99 g) and 1N-sodium hydroxide solution (5.65 ml) in methanol (50 ml) was stirred for 72 hours at room temperature. The mixture was evaporated in vacuo and the residue was dissolved in chloroform. The solution was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (14 g) with a mixture of chloroform and ethyl acetate (15:1) as an eluent to give 8-(2-methylbenzyloxy)-3-(1,2-propadienyl)-2-methylimidazo[1,2-a]pyridine (0.27 g). |
Here is a chemical reaction formula: Reactants are:m2:[OH-].[Na+];m1:Cl.C(C1=CC=CC=C1)OC=1C=2N(C=CC1)C(=C(N2)C)COCC#C, Reagents are:m3:O, and Products are 0:C(C1=CC=CC=C1)OC=1C=2N(C=CC1)C(=C(N2)C)COCC#C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 8-benzyloxy-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine hydrochloride (35.5 g) in hot water (700 ml) was neutralized with aqueous sodium hydroxide solution and extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate, treated with activated charcoal, and evaporated in vacuo. The residual solid was recrystallized from a mixture of methylene chloride and n-hexane to give 8-benzyloxy-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine (26.03 g). |
Here is a chemical reaction formula: Reactants are:m1_m3:SC1=NC2=C(N1CC(C1=NC=CC=C1)=O)C=CC=C2;m2:C(=O)([O-])[O-].[Na+].[Na+], Reagents are:, and Products are 0:N1=C(C=CC=C1)C1=CN2C(=NC3=C2C=CC=C3)S1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-mercapto-1-[2-oxo-2-(2-pyridyl)ethyl]benzimidazole (1 g.) in polyphosphoric acid was heated at 140° C. for 1 hour. The solution was neutralised with Na2CO3 solution and extracted into EtOAc (700 ml). The extracts were dried (MgSO4) and evaporated to give a solid which was recrystallised from EtOAc/EtOH to give the title compound (0.35 g.) mp 222°-4° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:ClC=1NC2=C(N1)C=CC=C2;m1_m2_m3:BrCC(=O)C1=NC=CC(=C1C)SCC;m1_m2_m3:C(=O)([O-])[O-].[K+].[K+], Reagents are:, and Products are 0:N1=CNC2=C1C=CC=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2-Chlorobenzimidazole is reacted with 2-bromoacetyl-4-ethylthio-3-methylpyridine in the presence of K2CO3 to give 2-chloro-1-[2-[4-ethylthio-3-methylpyridyl])-2-oxoethyl]benzimidazole. This is reacted with thiourea and treated with NH4OH to give 2-mercapto-1-(2-(2-(4-ethylthio-3-methylpyridyl))-2-oxoethyl)benzimidazole |
Here is a chemical reaction formula: Reactants are:m1_m3:C(C)SC1=C(C(=NC=C1)C1=CN2C(=NC3=C2C=CC=C3)S1)C;m2:ClC=1C=C(C(=O)OO)C=CC1, Reagents are:m1_m3:C(Cl)Cl, and Products are 0:C(C)SC1=C(C(=NC=C1)C1=CN2C(=NC3=C2C=CC=C3)S1=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-(4-ethylthio-3-methylpyrid-2-yl)-thiazolo[3,2-a]benzimidazole (0.01 mole) is dissolved in CH2Cl2 solution (100 ml) at 0° C. and treated with m-chloroperoxybenzoic acid (0.01 mole) for 0.5 hours. The solution is then washed with sodium carbonate solution and dried (MgSO4). Purification by chromatography on silica gives the title compound. |
Here is a chemical reaction formula: Reactants are:m4_m1_m2_m3:CC=1C=CC=C2C(=CNC12)SCC#N;m4_m1_m2_m3:[H-].[Al+3].[Li+].[H-].[H-].[H-];m4_m1_m2_m3:[Al+3].[Cl-].[Cl-].[Cl-], Reagents are:m4_m1_m2_m3:CCOCC, and Products are 0:NCCSC1=CNC2=C(C=CC=C12)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The ether solution was separated and dried over MgSO4. The filtered solution was evaporated in vacuo to give 24.4 g (66%) of 7-methylindol-3-ylthioacetonitrile as a tan solid. An ether solution of 14.1 g (70 mmole) of the nitrile was treated with 2.7 g (70 mmole) of lithium aluminum hydride and 9.5 g (70 mmole) of AlCl3. The dried ether solution was evaporated in vacuo to give 3-[(2-aminoethyl)thio]-7-methylindole which was crystalized from isopropanol to give 6.2 g of tan crystals. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2_m3_m6_m4:FC1=CC=C(CCl)C=C1;m1_m5_m2_m3_m6_m4:C(C)O;m1_m5_m2_m3_m6_m4:N1CCNCC1;m1_m5_m2_m3_m6_m4:C(C)O, Reagents are:m7:CCOCC, and Products are 0:FC1=CC=C(CN2CCNCC2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 29 g of p-fluorobenzyl chloride in 50 g of reagent ethanol was added dropwise to a stirred solution of 34.5 g of piperazine in 150 g of reagent ethanol. A cold water bath was used to maintain the reaction temperature at 20° C. during the addition. The reaction mixture was stirred for an additional 11/2 hours and then added to 2 liters of ether. Precipitated piperazine hydrochloride was filtered off. The filtrate was concentrated to an oil, which was chromatographed on a silica column, the eluant being a mixture of CH2Cl2 /methanol/ammonium hydroxide in the ratio of 45:5:1. After concentration of appropriate fractions, 21.7 g of 1-(4-fluorobenzyl)piperazine were isolated as a colorless liquid (56% of theory). |
Here is a chemical reaction formula: Reactants are:m4:[OH-].[Na+];m1_m2_m3_m5:ClC1=CC=C(CN2CCNCC2)C=C1;m1_m2_m3_m5:C(CC(=O)Cl)(=O)Cl;m1_m2_m3_m5:C(Cl)Cl, Reagents are:m1_m2_m3_m5:C(C)N(CC)CC, and Products are 0:O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)C(CC(=O)N2CCN(CC2)CC2=CC=C(C=C2)Cl)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4.2 g of 1-(4-chlorobenzyl)piperazine, 1.4 g of malonyl dichloride, 10 g of methylene chloride and 2.0 g of triethylamine was stirred for 60 hours. The reaction mixture was made basic with 2N sodium hydroxide. The organic layer was separated, and the aqueous phase was extracted with three 50 ml portions of ether, followed by three 50 ml portions of methylene chloride. The organic phases were combined and mixed with 100 ml of 2N hydrochloric acid. The aqueous phase was separated and made basic with 2N sodium hydroxide solution. The resulting oil was collected and chromatographed on silica, the eluant being CH2Cl2 /CH2OH/ammonium hydroxide (200:5:1). The appropriate fractions were combined, evaporated to an oil, dissolved in 100 ml of ether and precipitated with excess anhydrous hydrogen chloride. The precipitate was recrystallized from reagent ethanol to yield 1.3 g (22% of theory) of 1,3-bis[4-(4 -chlorobenzyl)-1-piperazinyl]-1,3-dioxopropane dihydrochloride monohydrate as a very slightly yellow crystalline solid (m.p. 199°-206° C.). |
Here is a chemical reaction formula: Reactants are:m1_m2:COC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC2=CC=C(C=C2)OC)C=C1;m1_m2:Br, Reagents are:m3:O, and Products are 0:OC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC2=CC=C(C=C2)O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4.5 g of 1,3-bis[4-(4-methoxybenzyl)-1-piperazinyl]propane from Example 19 and 125 ml of 49% hydrobromic acid was refluxed for 2 hours and was then cooled and diluted with 125 ml of water. After filtration the aqueous solution was neutralized with 2N sodium hydroxide to adjust the pH to 8. The resulting mixture was extracted three times each with 150 ml of ethanol. The alcohol was then removed by rotary evaporation and the residue was chromatographed on silica with the eluant being methylene chloride containing 1% ammonium hydroxide and 10% methanol to obtain 1.3 g (31% of theory) of 1,3-bis[4-(4-hydroxybenzyl)-1-piperazinyl]propane as a white crystalline product, melting at 197°-201° C. |
Here is a chemical reaction formula: Reactants are:m2:[OH-].[Na+];m1_m3:Cl.Cl.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC(C2=CC=CC=C2)C(=O)OCC)C=C1, Reagents are:m1_m3:C(C)O, and Products are 0:Cl.Cl.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCN2CCN(CC2)CC(C2=CC=CC=C2)C(=O)O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of 340 mg of 1-[4-(4-chlorobenzyl)-1-piperazinyl]-3-[4-(2-ethoxycarbonyl-2-phenylethyl)-1-piperazinyl]propane tetrahydrochloride in 10 ml of ethanol was treated with 1 ml of aqueous 5M sodium hydroxide and heated under reflux for 1 hour. The reaction mixture was evaporated to dryness under reduced pressure. The residue was mixed with lN hydrochloric acid (3 ml) and the resulting mixture extracted with ether (2×10 ml). The extract was discarded and the pH of aqueous phase adjusted to 5.5 with 1N hydrochloric acid. Aqueous saturated sodium chloride solution (10 ml) was added and the mixture extracted with butanol (2×10 ml). The butanol extract was filtered and treated with excess ethereal hydrogen chloride. The white precipitate was collected and recrystallized from aqueous ethanol to yield 1-[4-(4-chlorobenzyl)-1-piperazinyl]-3-[4-(2-carboxy-2-phenylethyl)-1-piperazinyl]propane tetrahydrochloride (140 mg, 40% yield) as a white crystalline solid (m.p. 230°-245° C. decomp.). |
Here is a chemical reaction formula: Reactants are:m1_m5:COC=1C=C(C=CC1OC)C1=CC(NC(=N1)C)=O;m2_m3:CC(C)([O-])C.[K+];m2_m3:CI;m4:O, Reagents are:m1_m5:CN(C=O)C, and Products are 0:COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 3,4-dihydro-6-(3,4 dimethoxyphenyl)-2-methylpyrimidin-4-one (2.0 g) in N,N-dimethylformamide (20 ml) were added potassium tert.butoxide (1.08 g) and methyl iodide (1.0 ml), and stirred at ambient temperature for an hour. Resulting mixture was poured into water, and extracted with ethyl acetate. The organic layer was chromatographed on silica gel eluting with chloroform to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-2,3-dimethylpyrimidin-4-one (1.38 g). |
Here is a chemical reaction formula: Reactants are:m1_m2:COC=1C=C(C=CC1OC)C1=CC(NC(=N1)C)=O;m1_m2:P(=O)(Cl)(Cl)Cl, Reagents are:, and Products are 0:ClC1=NC(=NC(=C1)C1=CC(=C(C=C1)OC)OC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidin-4-one (2.4 g) in phosphorus oxychloride (20 ml) was refluxed for 2 hours, and evaporated. To the residue were added aqueous sodium bicarbonate solution and chloroform, and stirred at ambient temperature for 2 hours. The organic layer was obtained and washed with water. After evaporated, the residue was dissolved in ethyl acetate-diisopropyl ether mixture (1:6 v/v). The precipitates were filtered off, and the filtrate was evaporated to give 4-chloro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine (2.09 g). |
Here is a chemical reaction formula: Reactants are:m1:C(C1=CC(OC)=C(OC)C=C1)(=O)CC(=O)OCC;m2_m3:NC1=NC=CC=C1, Reagents are:, and Products are 0:COC=1C=C(C=CC1OC)C=1N=C2N(C(C1)=O)C=CC=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Ethyl veratroylacetate (4.5 g) was added dropwise under stirring at 60°-70° C. to a suspension of 2-aminopyridine (0.84 g) in polyphosphoric acid (13.7 g). The reaction mixture was stirred at 100° C. for 3 hrs and poured into ice-water (50 ml). The aqueous solution was extracted with chloroform, washed with water, dried and evaporated to give dark oily residue which was chromatographed on silica gel using n-hexaneethyl acetate. The fractions were evaporated and the resulting residue was triturated with ethanol-isopropyl ether to give 2-(3,4-dimethoxyphenyl)-4-oxo-4H-pyrido[1,2-a]pyrimidine (3.8 g). |
Here is a chemical reaction formula: Reactants are:m1_m2:COC=1C=C(C=CC1OC)C1=CC(N(C(N1)=O)C)=NC1=C(C=C(C=C1C)C)C;m1_m2:P(=O)(Cl)(Cl)Cl, Reagents are:, and Products are 0:ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)-2-(1H)pyrimidone (5.0 g) was added phosphorus oxychloride (50 ml). The mixture was refluxed for 7 hours and evaporated under reduced pressure. The resulting syrup was triturated in a mixture of ice and water, neutralized with aqueous sodium bicarbonate and extracted with chloroform. The extract was dried and evaporated under reduced pressure. The residue was chromatographed on silica gel using chloroform to give 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (3.26 g). |
Here is a chemical reaction formula: Reactants are:m1_m2:ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC, Reagents are:m3:[Pd];m1_m2:C(C)O, and Products are 0:COC=1C=C(C=CC1OC)C1=CC(N(C=N1)C)=NC1=C(C=C(C=C1C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (1.5 g) in ethanol (20 ml) was added 10%-palladium on carbon (0.8 g). The mixture was stirred under hydrogen (1 atm) for 40 minutes. After removal of the catalist by filtration, the filtrate was evaporated in vacuo. The residue was neutralized with aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel using chloroform. The fractions containing the desired compound were combined and evaporated in vacuo to give a residue, which was recrystallized from ethyl acetate to afford 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (0.36 g). |
Here is a chemical reaction formula: Reactants are:m1_m3:ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC;m2:CNCC1=CC=CC=C1, Reagents are:m1_m3:C(C)O;m4:C(Cl)(Cl)Cl, and Products are 0:COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)N(CC1=CC=CC=C1)C)C)=NC1=C(C=C(C=C1C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (1.5 g) in ethanol (15 ml) was added N-methylbenzylamine (1.47 ml). The mixture was refluxed for 5 hours. The resulting suspension was dissolved in chloroform, washed with brine, dried over magnesium sulfate and evaporated in vacuo. The obtained syrup was triturated in diisopropyl ether and filtered to afford 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(N-methyl-N-benzylamino)-4-(2,4,6-trimethylphenylimino)pyrimidine (1.18 g). |
Here is a chemical reaction formula: Reactants are:m1_m3:ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC;m2:N1CCNCC1, Reagents are:m1_m3:C(C)O, and Products are 0:COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)N1CCNCC1)C)=NC1=C(C=C(C=C1C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (1.07 g) in ethanol (10 ml) was added piperazine (0.70 g). The mixture was refluxed for 3 hours, cooled to ambient temperature. The mixture was evaporated, and the residue was dissolved in chloroform and washed with aqueous sodium bicarbonate solution. The organic layer was dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel using a mixture of chloroform and methanol (95:5) to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(1-piperazinyl)-4-(2,4,6-trimethylphenylimino)pyrimidine (0.69 g). |
Here is a chemical reaction formula: Reactants are:m1_m3:ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC;m2:O.NN, Reagents are:m1_m3:C(Cl)(Cl)Cl, and Products are 0:COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)NN)C)=NC1=C(C=C(C=C1C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (10.0 g) in chloroform (100 ml) was added hydrazine hydrate (3.66 ml). The mixture was refluxed for 6 hours. The reaction mixture was evaporated in vacuo. The residue was chromatographed on silica gel using chloroform to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-2-hydrazino-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (3.46 g). |
Here is a chemical reaction formula: Reactants are:m2:C(=O)NN;m1_m3:ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC, Reagents are:m1_m3:C(Cl)(Cl)Cl, and Products are 0:COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)NNC=O)C)=NC1=C(C=C(C=C1C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (3.0 g) in chloroform (15 ml) was added formylhydrazine (1.36 g). The mixture was refluxed for 6 hours and cooled to ambient temperature. The resulting precipitates were filtered off and the filtrate was evaporated in vacuo. The residue was chromatographed on silica gel using chloroform to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-2-(2-formylhydrazino)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (0.84 g). |
Here is a chemical reaction formula: Reactants are:m1_m4:COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)N1CCNCC1)C)=NC1=C(C=C(C=C1C)C)C;m2_m3:C(C)N(CC)CC;m2_m3:FC1=CC=C(C(=O)Cl)C=C1, Reagents are:m1_m4:O1CCCC1, and Products are 0:COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)N1CCN(CC1)C(C1=CC=C(C=C1)F)=O)C)=NC1=C(C=C(C=C1C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(1-piperazinyl)-4-(2,4,6-trimethylphenylimino)pyrimidine (0.31 g) in tetrahydrofuran (10 ml) were added triethylamine (0.11 ml) and 4-fluorobenzoyl chloride (0.69 ml). The mixture was stirred at ambient temperature for an hour and the reaction was quenched by adding methanol (5 ml). After evaporation of the solvent, the residue was dissolved in ethyl acetate. The solution was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel using a mixture of chloroform and methanol (95:5) to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-2-[4-(4-fluorobenzoyl)piperazin-1-yl]-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (0.34 g). |
Here is a chemical reaction formula: Reactants are:m2:[N-]=[N+]=[N-].[Na+];m1:ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC, Reagents are:m3_m4:CO;m3_m4:O, and Products are 0:COC=1C=C(C=CC1OC)C1=CC(N(C=2N1N=NN2)C)=NC2=C(C=C(C=C2C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (1.0 g) in a mixture of methanol (9 ml) and water (1.5 ml) was added sodium azide (0.163 g). The mixture was stirred at 50° to 55° C. for an hour. After removal of the solvent, the residue was washed with water and collected by filtration to give 4,5-dihydro-7-(3,4-dimethoxyphenyl)-4-methyl-5-(2,4,6-trimethylphenylimino)tetrazolo[1,5-a]pyrimidine (0.80 g). |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)N(CC1=CC=CC=C1)C)C)=NC1=C(C=C(C=C1C)C)C;m1_m3_m2:CI, Reagents are:m1_m3_m2:O1CCCC1, and Products are 0:C(C1=CC=CC=C1)N=C1N(C(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(N-methyl-N-benzylamino)-4-(2,4,6-trimethylphenylimino)pyrimidine (1.0 g) in tetrahydrofuran (20 ml) was added methyl iodide (2.58 ml). The solution was refluxed for 10 hours and cooled to ambient temperature. The reaction mixture was evaporated in vacuo and the residue was chromatographed on silica gel using chloroform to give 2-benzylimino-6-(3,4-dimethoxyphenyl)-1,3-dimethyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine (0.62 g). |
Here is a chemical reaction formula: Reactants are:m1_m2:ClC1=NC(=NC(=C1)C1=CC(=C(C=C1)OC)OC)C;m1_m2:CC1=C(N)C(=CC(=C1)C)C, Reagents are:, and Products are 0:COC=1C=C(C=CC1OC)C1=CC(=NC(=N1)C)NC1=C(C=C(C=C1C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The mixture of 4-chloro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine (2.0 g) and 2,4,6-trimethylaniline (5.3 ml) was stirred at 120° C. for an hour. After cooled, the mixture was triturated with ethyl acetate. The precipitates were collected, and dissolved in chloroform. The solution was washed with aqueous sodium bicarbonate solution, dried over magnesium sulfate, and evaporated to give 6-(3,4-dimethoxyphenyl)-2-methyl-4-(2,4,6-trimethylphenylamino)pyrimidine (2.39 g). |
Here is a chemical reaction formula: Reactants are:m2:N1CCC=CC1;m1_m3:ClC1=NC(=CC(N1C)=NC1=C(C=C(C=C1C)C)C)C1=CC(=C(C=C1)OC)OC, Reagents are:m1_m3:C(C)O, and Products are 0:COC=1C=C(C=CC1OC)C1=CC(N(C(=N1)N1CCC=CC1)C)=NC1=C(C=C(C=C1C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (2.08 g) in ethanol (20 ml) was added 1,2,3,6-tetrahydropyridine (1.38 ml), and refluxed for 1.5 hours. The resulting precipitates were collected, dissolved in chloroform, washed with aqueous sodium bicarbonate solution, and dried over magnesium sulfate. After evaporated, the residue was triturated with diisopropyl ether to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(1,2,3,6-tetrahydropyridin-1-yl)-4-(2,4,6-trimethylphenylimino)pyrimidine (1.95 g). |
Here is a chemical reaction formula: Reactants are:m2:[BH4-].[Na+];m1:COC=1C=C(C=CC1OC)C1=CC(N(C=N1)C)=NC1=C(C=C(C=C1C)C)C, Reagents are:m3_m4:C(C)O;m3_m4:O, and Products are 0:COC=1C=C(C=CC1OC)C1=CC(N(CN1)C)=NC1=C(C=C(C=C1C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (2.0 g) in a mixture of ethanol (10 ml) and water (10 ml) was added sodium borohydride (1.04 g), and the mixture was stirred under reflux for 1.5 hours. After removal of the organic solvent, the mixture was suspended in water, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, evaporated, and triturated in ethanol, to give 6-(3,4-dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine (1.18 g). |
Here is a chemical reaction formula: Reactants are:m3:O;m1_m4_m2:COC=1C=C(C=CC1OC)C1=CC(N(CN1)C)=NC1=C(C=C(C=C1C)C)C;m1_m4_m2:C(C)(=O)OC(C)=O, Reagents are:m1_m4_m2:N1=CC=CC=C1, and Products are 0:C(C)(=O)N1CN(C(C=C1C1=CC(=C(C=C1)OC)OC)=NC1=C(C=C(C=C1C)C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 6-(3,4-dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine (0.5 g) in pyridine (5 ml) was added acetic anhydride (1.0 ml), and the mixture was stirred at ambient temperature for 2.5 hours. The mixture was poured into water (150 ml) and extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with chloroform to give 1-acetyl-6-(3,4-dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine (0.22 g). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:COC=1C=C(C=CC1OC)C1=CC(=NC(=N1)C)N1CCNCC1;m1_m4_m2_m3:C(C)N(CC)CC;m1_m4_m2_m3:ClC1=C(C(=O)Cl)C=C(C(=C1)Cl)S(N)(=O)=O, Reagents are:m1_m4_m2_m3:C(Cl)(Cl)Cl, and Products are 0:ClC1=C(C(=O)N2CCN(CC2)C2=NC(=NC(=C2)C2=CC(=C(C=C2)OC)OC)C)C=C(C(=C1)Cl)S(N)(=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 6-(3,4-dimethoxyphenyl)-2-methyl-4-(1-piperazinyl)pyrimidine (0.8 g) in chloroform (10 ml) were added triethylamine (0.39 ml) and 2,4-dichloro-5-sulfamoylbenzoyl chloride (0.74 g), and the mixture was stirred at ambient temperature for 20 hours. The reaction mixture was washed with water, dried over magnesium sulfate, and evaporated. The obtained mixture was chromatographed on silica gel eluting with chloroform-methanol mixture (49:1 v/v), to give 4-[4-(2,4-dichloro-5-sulfamoylbenzoyl)piperazin-1-yl]-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine (1.03 g). |
Here is a chemical reaction formula: Reactants are:m1_m5_m2:CC1=C(C(=CC(=C1)C)C)O;m1_m5_m2:[H-].[Na+];m4:O;m3:ClC1=NC(=NC(=C1)C1=CC(=C(C=C1)OC)OC)C, Reagents are:m1_m5_m2:CN(C=O)C, and Products are 0:COC=1C=C(C=CC1OC)C1=CC(=NC(=N1)C)OC1=C(C=C(C=C1C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 2,4,6-trimethylphenol (1.03 g) in N,N-dimethylformamide (20 ml) was added sodium hydride (60% in oil, 0.30 g), and stirred at ambient temperature for 5 minutes. To the solution was added 4-chloro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine (2.0 g), and the mixture was stirred at ambient temperature for 18 hours. The solution was poured into water (300 ml), and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel eluting with chloroform to give 6-(3,4-dimethoxyphenyl)-2-methyl-4-(2,4,6-trimethylphenoxy)pyrimidine (1.96 g). |
Here is a chemical reaction formula: Reactants are:m4:C(Cl)(Cl)Cl;m1_m5_m2_m3:NC1=CC=C(C=C1)NC1=NC(=NC(=C1)C1=CC(=C(C=C1)OC)OC)C;m1_m5_m2_m3:CS(=O)(=O)Cl;m1_m5_m2_m3:C(C)N(CC)CC, Reagents are:m1_m5_m2_m3:ClCCCl, and Products are 0:COC=1C=C(C=CC1OC)C1=CC(=NC(=N1)C)NC1=CC=C(C=C1)NS(=O)(=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 4-(4-aminophenylamino)-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine (1.0 g) in 1,2-dichloroethane (20 ml) were added methanesulfonyl chloride (0.28 ml) and triethylamine (0.83 ml) and the mixture was refluxed for 3 hours. After cooled, chloroform (50 ml) was added thereto, and washed with water. The solution was dried over magnesium sulfate, evaporated, and chromatographed on silica gel eluting with chloroform to give 6-(3,4-dimethoxyphenyl)-4-(4-mesylaminophenylamino)-2-methylpyrimidine (0.45 g). |
Here is a chemical reaction formula: Reactants are:m3:O;m1_m4_m2:COC=1C=C(C=CC1OC)C1=CC(N(CN1)C)=NC1=C(C=C(C=C1C)C)C;m1_m4_m2:CN=C=O, Reagents are:m1_m4_m2:N1=CC=CC=C1, and Products are 0:COC=1C=C(C=CC1OC)C1=CC(N(CN1C(NC)=O)C)=NC1=C(C=C(C=C1C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 6-(3,4-dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine (1.0 g) in pyridine (10 ml) was added methyl isocyanate (0.18 ml), and the mixture was stirred at ambient temperature for 3 hours. Then the mixture was poured into water (150 ml), and the resultant precipitates were collected. The precipitates were washed with water, and dried to give 6-(3,4-dimethoxyphenyl)-3-methyl-1-(N-methylcarbamoyl)-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine (0.99 g). |
Here is a chemical reaction formula: Reactants are:m1_m3_m4:C(C)(=O)NC1=C(CC=2SC=C(N2)C2=CC=NC=C2)C=CC=C1;m2:[OH-].[Na+], Reagents are:m1_m3_m4:Cl;m1_m3_m4:C(C)O;m5_m6:O;m5_m6:C(Cl)Cl, and Products are 0:NC1=C(CC=2SC=C(N2)C2=CC=NC=C2)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-(o-acetamidobenzyl)-4-(4-pyridyl)thiazole (2.30 g, 0.007 mol) in concentrated hydrochloric acid (2 mL) and ethanol (3 mL) was refluxed for 3 hours, allowed to cool, diluted with water (2 mL) and methylene chloride (5 mL), and basified with 2.5N sodium hydroxide. The layers were separated with the aqueous layer reextracted with chloroform (2x). The combined organic extracts were dried over potassium carbonate, concentrated, and chromatographed through a short column of silica gel to afford 2-(o-aminobenzyl)-4-(4-pyridyl)thiazole (1.30 g, 65%). mp. 179°-181° C. dec. |
Here is a chemical reaction formula: Reactants are:m3:[N+](=O)(O)[O-];m4:C([O-])([O-])=O.[Na+].[Na+];m1_m5_m2:C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC=NC=C1;m1_m5_m2:S(O)(O)(=O)=O, Reagents are:m1_m5_m2:C(Cl)(Cl)Cl, and Products are 0:[N+](=O)([O-])C1=CC=C(CC=2SC=C(N2)C2=CC=NC=C2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-benzyl-4-(4-pyridyl)thiazole (4.50 g, 0.018 mol) in chloroform (25 mL) was added dropwise to concentrated sulfuric acid (15 mL). The resulting mixture was cooled to 10° C. and fuming nitric acid (1.45 g, 0.97 mL) carefully added dropwise such that the reaction temperature did not exceed 40° C. The mixture was allowed to stir for thirty minutes, carefully neutralized with saturated sodium carbonate and the layers separated. The aqueous layer was reextracted with chloroform (2×25 mL) and the combined organic extracts were washed with brine (20 mL), dried over magnesium sulfate, and concentrated to afford a crude product (4.6 g). Several recrystallizations from hexane/ethyl acetate afforded pure 2-(p-nitrobenzyl)-4-(4-pyridyl)thiazole. mp. 140°-142° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m3:C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC=NC=C1;m1_m2_m5_m3:CN(CCN(C)C)C;m1_m2_m5_m3:C(CCC)[Li];m4:C(=O)OCC, Reagents are:m1_m2_m5_m3:O1CCCC1, and Products are 0:C1(=CC=CC=C1)C(C=O)C=1SC=C(N1)C1=CC=NC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 2-benzyl-4-(4-pyridyl)thiazole (4.00 g, 0.016 mol) and tetramethylethylenediamine (2.5 mL) in dry tetrahydrofuran (35 mL) at -78° C. under nitrogen atmosphere was added dropwise n-butyl lithium (1.6M in hexane, 11.4 mL). The resulting dark mixture was allowed to stir at -78° C. for 15 minutes, warmed to 0° C. for 2 hours, then cooled to -78° C. Ethyl formate (1.47 mL) was added dropwise and the mixture allowed to stir at -78° C. for 30 minutes then at 0° C. for one hour. The reaction mixture was quenched with methanol, concentrated, and chromatographed over silica gel. Recrystallization from hexane/ethyl acetate afforded 2-phenyl-2-[4-(4-pyridyl)-2-thiazolyl]acetaldehyde (1.76 g, 39%). mp. 163°-164° C. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:FC(C(=S)N)(C1=CC=CC=C1)F;m1_m3_m2:Br.BrCC(=O)C1=CC=NC=C1, Reagents are:m1_m3_m2:C(C)O, and Products are 0:FC(C1=CC=CC=C1)(F)C=1SC=C(N1)C1=CC=NC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 2,2-difluoro-2-phenylthioacetamide (1.57 g, 0.0092 mol) in 95% ethanol (20 mL) was added α-bromo-4-acetylpyridine hydrobromide (3.20 g, 0.012 mol) and the mixture warmed on a steam bath for thirty minutes. The product was isolated in the usual way and recrystallized from ethyl acetate/hexane to afford 1,1-difluoro-1-phenyl-[4-(4-pyridyl)-2-thiazolyl]methane (1.27 g, 48%). mp. 54.5°-55.5° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:OC=1SC=C(N1)C1=CC=NC=C1;m1_m2:P(=O)(Cl)(Cl)Cl, Reagents are:, and Products are 0:ClC=1SC=C(N1)C1=CC=NC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2-hydroxy-4-(4-pyridyl)thiazole (17.8 g, 0.10 mol) in phosphorous oxychloride (175 mL) was heated at 140° C. for 48 hours then quenched by carefully pouring onto ice (4000 mL). The resulting mixture was basified with 50% sodium hydroxide to pH 9 and extracted with methylene chloride (5×400 mL). The combined extracts were dried over sodium sulfate, concentrated, and chromatographed over silica gel (ethyl acetate as eluant). Recrystallization from ethyl acetate/hexane afforded 2-chloro-4-(4-pyridyl)thiazole (5.70 g, 29%). mp. 124°-125° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:ClC=1SC=C(N1)C1=CC=NC=C1;m1_m2_m4_m3:C(C1=CC=CC=C1)C#N;m1_m2_m4_m3:[NH2-].[Na+], Reagents are:m1_m2_m4_m3:C1(=CC=CC=C1)C, and Products are 0:C1(=CC=CC=C1)C(C#N)C=1SC=C(N1)C1=CC=NC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 2-chloro-4-(4-pyridyl)thiazole (1.00 g, 0.005 mol) and benzylcyanide (1.18 g, 0.010 mol) in dry toluene (10 mL) at 5° C. was added sodamide (400 mg, 0.010 mol) and the mixture heated to 100° C. for 20 minutes. After cooling, the mixture was quenched with water, the layers separated, and the aqueous phase washed with methylene chloride (2×50 mL). The combined extracts were dried over sodium sulfate, concentrated, and chromatographed through silica gel (3:1 ethyl acetate/methylene chloride as eluant). After decolorizing with charcoal, recrystallization from hexane/ethyl acetate afforded 2-phenyl-2-[4-(4-pyridyl)-2-thiazolyl]acetonitrile (115 mg, 8%). mp. 110°-111° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC=NC=C1;m1_m2_m3_m4:[Mn](=O)(=O)(=O)[O-].[K+], Reagents are:m1_m2_m3_m4:C1=CC=CC=C1;m1_m2_m3_m4:O;m5:[I-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC, and Products are 0:C1(=CC=CC=C1)C(=O)C=1SC=C(N1)C1=CC=NC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 2-benzyl-4-(4-pyridyl)thiazole (3.00 g, 0.01 mol) and potassium permanganate (3.16 g, 0.02 mol) in benzene (30 mL) and water (60 mL) was added tetrahexyl ammonium iodide (0.96 g, 0.02 mol). The biphasic mixture was heated at reflux for 15 hours. After cooling the organic layer was separated and concentrated. The residue was taken up in ethyl acetate, filtered through silica gel, concentrated and chromatographed (ethyl acetate/hexane as eluant). Recrystallization from ethyl acetate/hexane afforded 1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanone (0.50 g, 11%). mp. 135°-136° C. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:C1(=CC=CC=C1)C(=O)C=1SC=C(N1)C1=CC=NC=C1;m1_m3_m2:[BH4-].[Na+], Reagents are:m1_m3_m2:CO, and Products are 0:C1(=CC=CC=C1)C(O)C=1SC=C(N1)C1=CC=NC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanone (675 g, 0.0025 mol) in methanol (40 mL) was added sodium borohydride (300 mg, 0.0079 mol) in portions and the mixture allowed to stir at room temperature for one hour. The reaction mixture was concentrated, diluted with water, and extracted with ether (3×25 mL). The combined extracts were washed with brine, dried over magnesium sulfate, concentrated, and chromatographed. Recrystallization from hexane/ethyl acetate afforded 1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanol (300 mg, 45%). mp. 146°-147° C. |
Here is a chemical reaction formula: Reactants are:m1_m4:ClC1=CC(=CC=C1)C(=O)OO;m3:ClC1=CC(=CC=C1)C(=O)OO;m2_m5:C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC=NC=C1, Reagents are:m1_m4:C(Cl)Cl;m2_m5:C(Cl)Cl, and Products are 0:C1(=CC=CC=C1)CC=1SC=C(N1)C1=CC=[N+](C=C1)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of m-chloroperbenzoic acid (14.5 g) in dry methylene chloride (150 mL) was added a solution of 2-benzyl-4-(4-pyridyl)thiazole (15.1 g, 0.06 mol) in methylene chloride (125 mL) over thirty minutes. The mixture was allowed to stir overnight at room temperature then an additional portion of m-chloroperbenzoic acid (3.00 g) was added. After an additional six hours of stirring the mixture was extracted with saturated sodium bicarbonate (3×100 mL). The organic layer was dried over sodium sulfate, and concentrated to a total volume of 75 mL. Dilution with ether (200 mL) afforded 4-[2-(phenylmethyl)-4-thiazolyl]pyridine-1-oxide (15.3 g, 95%). Recrystallization from ethanol/ether afforded an analytical sample. mp. 170°-172° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C1(=CC=CC=C1)CC=1SC=C(N1)C1=CC=[N+](C=C1)[O-];m1_m2:P(=O)(Cl)(Cl)Cl, Reagents are:, and Products are 0:C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC(=NC=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of 4-[2-(phenylmethyl)-4-thiazolyl]pyridine-1-oxide (1.00 g, 0.0037 mol) in phosphorous oxychloride (10.0 g) was warmed on a steam bath overnight. After cooling the reaction mixture was concentrated and the residue treated with an excess of aqueous sodium bicarbonate. The tan precipitate was collected, taken up in methylene chloride (15 mL) and ether (75 mL), and filtered through celite. The filtrate was concentrated to a total volume of 10 mL and diluted with hexane (50 mL). The product which crystallized on standing was collected and dried to afford 2-benzyl-4-(2-chloro-4-pyridyl)thiazole (325 mg, 31%). mp. 104°-106° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC(=NC=C1)Cl, Reagents are:m1_m2:N1CCCCC1, and Products are 0:Cl.Cl.C(C1=CC=CC=C1)C=1SC=C(N1)C1=CC(=NC=C1)N1CCCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-benzyl-4-(2-chloro-4-pyridyl)thiazole (1.00 g, 0.0035 mol) in piperidine (15 mL) was heated to reflux for 16 hours. The reaction mixture was concentrated, taken up in ether (50 mL), filtered through celite, and the filtrate washed with water (2×). The ether layer was dried and concentrated. The residue was taken up in ethanol (20 mL) and treated with an excess of dry hydrochloric acid. Careful dilution with ether afforded 2-benzyl-4-[2-(1-piperidyl)-4-pyridyl]thiazole dihydrochloride (525 mg, 49%). mp. 145° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3_m5:Cl.NN1CCC=CC1;m1_m2_m4_m3_m5:C(C)N(CC)CC;m1_m2_m4_m3_m5:ClC(=O)OC1=CC=CC=C1, Reagents are:m1_m2_m4_m3_m5:C(Cl)Cl;m1_m2_m4_m3_m5:C(Cl)Cl, and Products are 0:O(C1=CC=CC=C1)C(=O)NN1CCC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of N-amino-1,2,3,6-tetrahydropyridine hydrochloride (1.346 g) and triethylami-ne (2.024 g) in methylene chloride (60 ml) was added a solution of phenyl chloroformate (1.566 g) in methylene chloride (40 ml) and the mixture was stirred for 4 hours at 5° C. Evaporation of the solvent gave a residue, which was extracted with ethyl acetate (150 ml). The extract was washed with water and dried over magnesium sulfate. The solvent was evaporated in vacuo to give N-(phenoxy- carbonylamino)-1,2,3,6-tetrahydropyridine (2.01 g), which was recrystallized from diisopropyl ether to give the desired compound (0.732 g) as colorless needles. mp: 124°-125.5° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3_m5:Cl.NN1CCC=CC1;m1_m2_m4_m3_m5:C(C)N(CC)CC;m1_m2_m4_m3_m5:FC=1C=C(C=CC1)N=C=O, Reagents are:m1_m2_m4_m3_m5:C(Cl)Cl;m1_m2_m4_m3_m5:C(Cl)Cl, and Products are 0:FC=1C=C(C=CC1)NC(=O)NN1CCC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of N-amino-1,2,3,6-tetrahydropyridine hydrochloride (1.346 g) and triethylamine (1.012 g) in dry methylene chloride (40 ml) was added a solution of 3-fluorophenyl isocyanate (1.37 g) in dry methylene chloride under ice-bath cooling. After stirring for one hour, the reaction mixture was evaporated to dryness. The residue was extracted with ethyl acetate (100 ml). The extract was washed with water, evaporated to dryness and recystallized from ethyl acetate to give N-[[(3-fluorophenyl)carbamoyl]amino]-1,2,3,6-tetrahydropyridine (1.43 g). mp: 136.5°-138.5° C. |
Here is a chemical reaction formula: Reactants are:m2:[OH-].[Na+];m1_m4_m5:Cl.NN1CCC(=CC1)C1=CC=CC=C1;m3_m6:FC1=CC=C(C=C1)N=C=S, Reagents are:m1_m4_m5:O1CCOCC1;m1_m4_m5:O;m3_m6:O1CCOCC1, and Products are 0:FC1=CC=C(C=C1)NC(=S)NN1CCC(=CC1)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 N-amino-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride (1.05 g) in a mixture of dioxane (10 ml) and water (5 ml) was added 1N sodium hydroxide solution (5 ml) under ice-bath cooling, and then a solution of 4-fluorophenyl isothiocyanate (1.15 g) in dioxane (5 ml) was added thereto. The mixture was stirred for 5 hours under ice-bath cooling. The reaction mixture was evaporated in vacuo and the residue was extracted several times with ethyl acetate. The combined extract was washed with water, dried over magnesium sulfate and evaporated in vacuo to give a crude product, which was recrystallized from ethyl acetate to give N-[[(4-fluorophenyl)thiocarbamoyl]amino]-4-phenyl-1,2,3,6-tetrahydropyridine (1.05 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:FC1=CC=C(NC(=O)OC2=CC=CC=C2)C=C1;m1_m2_m3_m4:Cl.NN1CCC=CC1;m1_m2_m3_m4:C(C)N(CC)CC, Reagents are:m1_m2_m3_m4:C(Cl)(Cl)Cl, and Products are 0:FC1=CC=C(C=C1)NC(=O)NN1CCC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 4-fluoro-N-phenoxycarbonylaniline (2.29 g), N-amino-1,2,3,6-tetrahydropyridine hydrochloride (1.346 g) and triethylamine (1.02 g) in chloroform (25 ml) was refluxed for 20 hours. After evaporation of chloroform, the residue was extracted with ethyl acetate (100 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (20 g) using chloroform as an eluent to give N-[[(4-fluorophenyl)carbamoyl]amino]-1,2,3,6-tetrahydropyridine (1.05 g). mp: 156°-157° C. |
Here is a chemical reaction formula: Reactants are:m1_m4_m5:C1(=CC=CC=C1)NC(=O)N=[N+]1CC=CC=C1;m3:Cl;m2:[BH4-].[Na+], Reagents are:m1_m4_m5:C(C)O;m1_m4_m5:O, and Products are 0:C1(=CC=CC=C1)NC(=O)NN1CCC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of N-(phenylcarbamoylimino)pyridinium ylide (0.64 g) in a mixture of ethanol (30 ml) and water (10 ml) was added sodium borohydride (0.20 g) at ambient temperature. After being stirred for 4 hours, the reaction mixture was acidified with 1N hydrochloric acid, concentrated to a volume of ca. 15 ml. The crystalline precipitate was collected, washed with water and dried in vacuo. The crude product was dissolved in ethyl acetate and extracted with 10% hydrochloric acid (20 ml). The extract was adjusted to pH 3 with aqueous sodium bicarbonate and extracted with ethyl acetate (30 ml). The organic layer was washed with aqueous sodium bicarbonate (10 ml), dried over magnesium sulfate and evaporated to give N-(phenylcarbamoylamino)-1,2,3,6-tetrahydropyridine (0.28 g), which was recrystallized from ethyl acetate to afford colorless needles (0.15 g). mp: 157°-159° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5:FC1=CC=C(C=C1)NC(=O)N=[N+]1CC=CC=C1;m1_m2_m5:[BH4-].[Na+];m3:[BH4-].[Na+];m4:O, Reagents are:m1_m2_m5:C(C)O, and Products are 0:FC1=CC=C(C=C1)NC(=O)NN1CCC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of N-[[(4-fluorophenyl)carbamoyl]-imino]pyridinium ylide (1.04 g) and sodium borohydride (2.55 g) in ethanol (100 ml) was stirred at ambient temperature for 16 hours. Excess of sodium borohydride was decomposed with water, and the resulting mixture was evaporated. The residue was extracted with chloroform (20 ml×3). The combined organic extract was washed with water, dried over magnesium sulfate and evaporated to give crystalls. Recrystallization from diisopropyl ether gave N-[[(4-fluorophenyl)-carbamoyl]amino]-1,2,3,6-tetrahydropyridine (0.60 g). |
Here is a chemical reaction formula: Reactants are:m2:[OH-].[Na+];m1_m3_m4:COC(=O)C1=CC=C(C=C1)NC(=O)NN1CCC=CC1, Reagents are:m1_m3_m4:CO;m1_m3_m4:C(Cl)(Cl)Cl, and Products are 0:C(=O)(O)C1=CC=C(C=C1)NC(=O)NN1CCC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of N-[[(4-methoxycarbonylphenyl)-carbamoyl]amino]-1,2,3,6-tetrahydropyridine (1.21 g) in a mixture of methanol (30 ml) and chloroform (30 ml) was added. 1N sodium hydroxide (10 ml) and the mixture was stirred at ambient temperature for 18 hours. After evaporation of the solvent, the residue was extracted with chloroform (20 ml×3). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (40 g) eluting with chloroform, to give N-[[(4-carboxyphenyl)-carbamoyl]amino]-1,2,3,6-tetrahydropyridine (0.65 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)(C)(C)OC([C@H]1N(CCC1)C([C@@H](N[C@@H](CC(=O)C1=CC=CC=C1)C(=O)OCC)C)=O)=O, Reagents are:m1_m2_m3:C(C)O;m1_m2_m3:[Pd], and Products are 0:C(C)(C)(C)OC([C@H]1N(CCC1)C([C@@H](N[C@@H](C[C@@H](O)C1=CC=CC=C1)C(=O)OCC)C)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 13.4 g (30 mmoles) of N-[1-(S)-ethoxycarbonyl-3-phenyl-3-oxo-propyl]-(S)-alanyl-(S)-proline-t - butylester are dissolved in 120 ml of ethanol and hydrogenated in the presence of 1.5 g of 10% palladium-on-charcoal catalyst at room temperature. After the uptake of the theoretically needed hydrogen (720 ml), the catalyst is filtered off. A mixture of N-[1-(S)-ethoxycarbonyl-3-phenyl-3(S)-hydroxypropyl]-(S)-alanyl-(S)-proline-t-butylester and N-[1-(S)-ethoxycarbonyl-3-phenyl-3(R)-hydroxypropyl]-(S)-alanyl-(S)-proline-t-butylester is obtained. |
Here is a chemical reaction formula: Reactants are:m1_m4:C(C)(C)(C)OC([C@H]1N(CCC1)C([C@@H](N)C)=O)=O;m2:C(C)OC(\C=C\C(C1=CC=CC=C1)=O)=O;m3:C(\C=C/C(=O)O)(=O)O, Reagents are:m1_m4:C1=CC=CC=C1, and Products are 0:C(\C=C/C(=O)O)(=O)O.C(C)(C)(C)OC([C@H]1N(CCC1)C([C@@H](N[C@@H](CC(=O)C1=CC=CC=C1)C(=O)OCC)C)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4.84 g (20 mmoles) of (S)-alanyl-(S)-proline-t-butylester are dissolved in 40 ml of dry benzene and 4.08 g (20 mmoles) of E-ethyl-3-benzoyl-acrylate are added at room temperature under stirring. After one hour stirring at room temperature the solvent is evaporated off under reduced pressure, the residue is dissolved in 20 ml of ethyl acetate and 2.32 g (20 mmoles) of maleinic acid are added. The precipitated crystals are filtered off after one hour standing and washed with 20 ml of ethyl acetate. 6.7 g (60%) of product are obtained with a melting point of 109°-110° C. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(C)(C)OCC(=O)OCCCC;m3_m1:C([O-])([O-])=O.[K+].[K+], Reagents are:m3_m1:CO.O, and Products are 0:C(C)(C)(C)OCC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 100 ml of a 50:50 (v/v) methanol/water solution containing 14.35 g of potassium carbonate, was added n-butyl 2-tert-butoxyacetate (6.50 g, 0.0346 mol). The mixture was heated at reflux for 17 hours and the volatiles removed on a flash evaporator. The remaining solution was cooled to approximately 0° C. and acidified to pH 3-4 with cold 50% aqueous hydrogen chloride. The product was extracted with ether, the ether extract washed with brine and dried over magnesium sulfate, then concentrated in vacuo to give the title compound as a yellow liquid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5_m6:ClCC1=NC2=CC=CC=C2C=C1;m1_m2_m3_m4_m5_m6:C1(=CC=CC=C1)O;m1_m2_m3_m4_m5_m6:C([O-])([O-])=O.[K+].[K+];m1_m2_m3_m4_m5_m6:C([O-])([O-])=O.[Cs+].[Cs+];m1_m2_m3_m4_m5_m6:[I-].[Na+], Reagents are:m1_m2_m3_m4_m5_m6:CC(=O)C, and Products are 0:O(C1=CC=CC=C1)CC1=NC2=CC=CC=C2C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2-chloromethyl quinoline (0.05 mol), phenol (0.055 mol), finely powdered potassium carbonate (0.055 mol), cesium carbonate (0.005 mol) and sodium iodide (0.0025 mol) in acetone was refluxed for about 4 hours. The reaction mixture was cooled to room temperature and filtered and the filtrate was concentrated and dissolved in ether. The ether solution was washed thoroughly with lN NaOH solution, water and brine. After drying the ether solution over anhydrous magnesium sulfate, and filtering off the drying agent, the solvent was evaporated off to leave the crude product which was crystallized from hexane and ether to yield the desired compound as a light yellow solid, m.p. 79.5°-80.5° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:FC=1C=C2C=3C(CCCC3NC2=CC1)=O;m1_m2_m4_m3:C([O-])([O-])=O.[K+].[K+];m1_m2_m4_m3:COS(=O)(=O)OC, Reagents are:m1_m2_m4_m3:CC(=O)C, and Products are 0:FC=1C=C2C=3C(CCCC3N(C2=CC1)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The product of Stage (ii) (7.28 g), potassium carbonate (9.90 g), acetone (70 ml), and dimethylsulphate (5.1 ml) were vigorously stirred at room temperature overnight under nitrogen. The mixture was concentrated to one half of its volume and then stirred with water (350 ml) for 30 min. The mixture was filtered off, washed with water (50 ml), air-dried for 1 h, and dried in vacuo over phosphorus pentoxide to give the title compound as needles (7.59 g), m.p. 157.5°-158.5°. |
Here is a chemical reaction formula: Reactants are:m2:O;m1:BrC1=CC=C(C=C1)NN=C1CC(CCC1)=O, Reagents are:m4_m3:C(C)(=O)O;m4_m3:[Cl-].[Zn+2].[Cl-], and Products are 0:BrC=1C=C2C=3C(CCCC3NC2=CC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The product of Stage (i) (1.5 g) was heated under reflux with dry zinc chloride (16 g) in glacial acetic acid (75 ml) for 24 h. The mixture was cooled, poured into water (200 ml), and the resulting solid filtered off and dried (0.95 g). Purification by flash chromatography (E) gave the title compound as a solid (125 mg). T.l.c. (F), Rf 0.65 |
Here is a chemical reaction formula: Reactants are:m4:O;m1_m2_m3_m5:C=O;m1_m2_m3_m5:Cl.CNC;m1_m2_m3_m5:BrC=1C=C2C=3C(CCCC3N(C2=CC1)C)=O, Reagents are:m1_m2_m3_m5:C(C)(=O)O, and Products are 0:Cl.BrC=1C=C2C=3C(C(CCC3N(C2=CC1)C)CN(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Paraformaldehyde (1.5 g) and dimethylamine hydrochloride (3.75 g) were added to a solution of the product of Stage (iii) (10 g) in acetic acid (70 ml) and then heated to reflux for 8 h. On cooling to ambient temperature the reaction mixture was poured into water (400 ml). The oil which separated out was triturated with ether (500 ml) to give a solid (9 g) which was partitioned between ethyl acetate (2×30 ml) and saturated aqueous sodium carbonate (100 ml). The organic phase was evaporated and the residue purified by flash chromatography (G) to give the pure free base as a solid (0.40 g). A sample (0.4 g) was dissolved in ethanol (10 ml), filtered, and ethereal HCl (6 ml) was added. On addition of dry ether (20 ml), the title compound crystallized as a solid (0.38 g) m.p. 219°-220°. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C1(CC(CCC1)=O)=O;m1_m2_m3_m4:Cl.COC1=CC=C(C=C1)NN, Reagents are:m5:O;m1_m2_m3_m4:C(C)O;m1_m2_m3_m4:O, and Products are 0:COC=1C=C2C=3C(CCCC3NC2=CC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,3-Cyclohexanedione (8 g) was added to a solution of 4-methoxyphenylhydrazine hydrochloride (10 g) in ethanol (350 ml) and water (70 ml). The resulting solution was stirred at room temperature for 3 h and then at reflux for 14 h. On cooling to ambient temperature, the reaction mixture was poured into water (3 l) to give a solid, which was dried in vacuo to give the title compound, (6.0 g) m.p. 279°-279.5°. |
Here is a chemical reaction formula: Reactants are:m3:S(=O)(=O)(OC)OC;m1_m2_m5:C([O-])([O-])=O.[K+].[K+];m1_m2_m5:COC=1C=C2C=3C(CCCC3NC2=CC1)=O;m4:O, Reagents are:m1_m2_m5:CC(=O)C, and Products are 0:COC=1C=C2C=3C(CCCC3N(C2=CC1)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Anhydrous potassium carbonate (2.24 g) was added to a solution of the product of Stage (i) (3 g) in acetone (30 ml) at room temperature and stirred for 30 min. Dimethyl sulphate (1.6 ml) was added and the mixture was heated to reflux for 4 h. The resulting solution was poured into water (150 ml) and the resulting precipitate filtered off to give the title compound as a solid (2.5 g), m.p. 150°-151°. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C1(CC(CCC1)=O)=O;m1_m2_m3_m4:Cl.C1(=CC=CC=C1)COC1=CC=C(C=C1)NN, Reagents are:m5:O;m1_m2_m3_m4:C(C)O;m1_m2_m3_m4:O, and Products are 0:C1(=CC=CC=C1)COC=1C=C2C=3C(CCCC3NC2=CC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,3-Cyclohexanedione (3.1 g) and the product of Stage (i) (5.6 g) in ethanol (196 ml) and water (39 ml) was stirred at room temperature for 3 h and then heated to reflux for 14 h. The resulting solution was allowed to cool, poured into water (500 ml) and the precipitate filtered and washed with isopropyl acetate and ether to give a solid. Recrystallisation from methanol gave the title compound as a solid (2.5 g) m.p. 235°-237°. |
Here is a chemical reaction formula: Reactants are:m1_m4:COC=1C=C(N)C=CC1;m1_m4:Cl;m3_m5:[Sn];m3_m5:Cl;m2_m6:N(=O)[O-].[Na+], Reagents are:m2_m6:O, and Products are 0:Cl.COC=1C=C(C=CC1)NN, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of 3-methoxyaniline (10 g) in concentrated hydrochloric acid (85 ml) was stirred at ca. 0° and a solution of sodium nitrite (5.75 g) in water (25 ml) was slowly added over a period of 30 min keeping the temperature of the mixture at ca. 0°. After 1 h a solution of tin II chloride dihydrate (59 g) in concentrated hydrochloric acid (50 ml) was added over a period of 1.5 h, to the cooled suspension keeping the temperature below 0° C. The suspension was stirred for a further 30 min, filtered and washed with dried ether to give the title compound as a solid (14 g) m.p. 171°. |
Here is a chemical reaction formula: Reactants are:m4:O;m1_m5_m2_m6:OC1=CC=C(CC2C(NC(S2)=O)=O)C=C1;m1_m5_m2_m6:[H-].[Na+];m3_m7:ClCC=1N=C(OC1)C1=CC=CC=C1, Reagents are:m1_m5_m2_m6:CN(C=O)C;m3_m7:CN(C=O)C, and Products are 0:C1(=CC=CC=C1)C=1OC=C(N1)COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 5-(4-hydroxybenzyl)-2,4-thiazolidinedione (9.4 g) in N,N-dimethylformamide (80 ml) was added 60% sodium hydride in oil (3.4 g), and the mixture was stirred for 30 minutes. Then, a solution of 4-chloromethyl-2-phenyloxazole (9.6 g) in N,N-dimethylformamide (20 ml) was added dropwise thereto at room temperature. After being stirred at 70° C. for 1 hour, the reaction solution was poured into water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated to give 5-[4-(2-phenyl-4-oxazolylmethoxy)benzyl]-2,4-thiazolidinedione (9.1 g, 47.4%). Recrystallization from ethanol yielded colorless needles. m.p. 188°-189° C. Elemental analysis for C20H16N2O4S; Calcd.: C, 63.15; H, 4.24; N, 7.36. Found: C, 63.19; H, 4.16; N, 7.23. |
Here is a chemical reaction formula: Reactants are:m4:O;m1_m5_m2_m6:[H-].[Na+];m1_m5_m2_m6:OC1=CC=C(CC2C(NC(S2)=O)=O)C=C1;m3_m7:ClCC=1N=C(OC1)C1(CCCCC1)C, Reagents are:m1_m5_m2_m6:CN(C=O)C;m3_m7:CN(C=O)C, and Products are 0:CC1(CCCCC1)C=1OC=C(N1)COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 60% sodium hydride in oil (1.32 g) was added to solution of 5-(4-hydroxybenzyl)-2,4-thiazolidinedione (3.35 g) in N,N-dimethylformamide (30 ml), and the mixture was stirred for 30 minutes. Then, solution of 4-chloromethyl-2-(1-methylcyclohexyl)oxazole (3.85 g) in N,N-dimethylformamide (5 ml) was added dropwise thereto at room temperature. After being stirred at 60° C. for 1 hour, the reaction solution was poured into water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The oily residue was chromatographed on a column of silica gel (70 g). Elution with hexaneethyl acetate (2:1, V/V) gave 5-{4-[2-(1-methylcyclohexyl)-4-oxazolylmethoxy]benzyl}-2,4-thiazolidinedione as an oily substance. A solution of sodium 2-ethylhexanoate in isopropanol (2N, 3 ml) was added to the oily substance, and treated with ether. The crystals which separated out were collected by filtration to give 5- {4-[2-(1-methylcyclohexyl)-4-oxazolylmethoxy]benzyl}-2,4-thiazolidinedione.sodium salt (2.3 g, 36.3%). Recrystallization from methanol afforded colorless plates. m.p. 285°-287° C. (decomp.) Elemental analysis for C21H23N2O4SNa, Calcd.: C, 59.70; H, 5.49; N, 6.63. Found: C, 59.76; H, 5.56; N, 6.82. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:N=C1SC(C(N1)=O)CC1=CC=C(C=C1)OCCC=1N=C(OC1C)C1=CC=CC=C1;m1_m2_m3:Cl;m1_m2_m3:C(C)O, Reagents are:, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2-imino-5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-4-thiazolidinone (18.8 g), 2N-HCl (200 ml) and ethanol (200 ml) was heated under reflux for 12 hours. The solvent was distilled off under reduced pressure. The residue was neutralized with saturated aqueous solution of sodium hydrogen carbonate, and extracted with chloroform. The chloroform layer was washed with water and dried (MgSO4). The solvent was distilled off, whereby 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-2,4-thiazolidinedione (18.0 g, 95.7%) was obtained. Recrystallization from ethanol afforded colorless needles. m.p. 113°-114° C. Elemental Analysis for C22H20N2O4S, Calcd.: C, 64.69; H, 4.93; N, 6.86. Found: C, 64.48; H, 4.91; N, 6.75. |
Here is a chemical reaction formula: Reactants are:m2_m3:OS(=O)(=O)O;m2_m3:O1CCOCC1;m1:N=C1SC(C(N1)=O)CC1=CC=C(C=C1)OCC=1N=C(OC1C)C1=CC=CC=C1, Reagents are:m4:O, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2-imino-5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-thiazolidinone (11.4 g), 1N.H2SO4 (100 ml) and dioxane (100 ml) was stirred at 80° C. for 5 hours, and poured in water. The aqueous mixture was extracted with chloroform. The chloroform layer was washed with water, dried (MgSO4) and concentrated. The oily residue was chromatographed on a column of silica gel (200 g), and from the fractions eluted with chlorform-methanol (100:1, V/V), there was obtained 5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-2,4-thiazolidinedione (6.7 g, 58.8%). Recrystallization from ethyl acetate-hexane afforded colorless plates. m.p. 162°-163° C. Elemental analysis for C21H18N2O4S, Calcd.: C, 63.95; H, 4.60; N, 7.10. Found: C, 63.84; H, 4.63; N, 6.90. This product showed the IR and NMR spectra in accordance with those of the compound obtained in Example 6. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:BrN1C(CCC1=O)=O;m1_m2_m3_m4:CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1;m1_m2_m3_m4:N(=NC(C#N)(C)C)C(C#N)(C)C, Reagents are:m1_m2_m3_m4:C(Cl)(Cl)(Cl)Cl, and Products are 0:BrCC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: N-Bromosuccinimide (2.75 g) was added portionwise to a solution of 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-2,4-thiazolidinedione (6.0 g) and α,α'-azobisisobutyronitrile (0.5 g) in carbon tetrachloride(150 ml) under reflux. After refluxing for another 10 minutes, the reaction mixture was washed with water and dried (MgSO4). The solvent was distilled off to give 5-{4-[2-(5-bromomethyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-2,4-thiazolidinedione as a crude oily substance (about 8 g). IR (neat) cm-1 : 1750, 1690. NMRδ(ppm) in CDCl3 : 3.03 (2 HtJ=7 Hz), 2.9 to 3.2 (1H, m), 3.48 (1H, d.d, J=14 and 5 Hz), 4.24 (2H, t, J=7 Hz), 4.45 (1h, d.d, J=9 and 5 Hz), 4.61 (2H, s), 6.81 (2H, d, J=9 Hz), 7.10 (2H, d, J=9 Hz), 7.4 (3H, m), 8.0 (2H, m), 8.70 (1H, broad s). |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:C(C)(=O)OC(C)=O;m1_m2_m4:CC=1OC(=C(N1)C(COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1)O)C;m3:O, Reagents are:m1_m2_m4:CS(=O)C, and Products are 0:CC=1OC(=C(N1)C(COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Acetic anhydride (1.0 ml) was added to a solution of 5-{4-[2-(2,5-dimethyl-4-oxazolyl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione (0.5 g) in dimethylsulfoxide (10 ml), and the mixture was allowed to stand overnight and poured into water. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concetrated. The oily residue was chromatographed on a column of silica gel (40 g), and from the fractions eluted with benzene-acetone (9:1 V/v), there was obtained 5-{4-[2-(2,5-dimethyl-4-oxazolyl)-2-oxoethoxy]benzyl}-2,4-thiazolidinedione (0.24 g, 48.3%). Recrystallization from ethyl acetate-hexane afforded colorless plates, m.p. 161°-162° C. Elemental analysis for C17H16N2O5S, Calcd.: C, 56.66; H, 4.47; N, 7.77. Found: C, 56.62; H, 4.38; N, 7.60. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C=O)C=C1;m1_m2_m3_m4:S1C(NC(C1)=O)=O;m1_m2_m3_m4:N1CCCCC1, Reagents are:m1_m2_m3_m4:C(C)O, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde (5.0 g), 2,4-thiazolidinedione (3.8 g), piperidine (0.32 ml) and ethanol (100 ml) was stirred under reflux for 5 hours. After cooling, the crystals which separated out were collected by filtration to give 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione (5.1 g, 76.8%). Recrystallization from chloroform-ethanol afforded colorless needles, m.p. 213°-214° C. Elemental analysis for C22H18N2O4S, Calcd.: C, 65.01; H, 4.46; N, 6.89. Found: C, 64.81; H, 4.55; N, 6.78. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2_m6:[H-].[Na+];m1_m5_m2_m6:OC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1;m3_m7:ClCC=1N=C(OC1C)C1=CC=CC=C1;m4:O, Reagents are:m1_m5_m2_m6:CN(C=O)C;m8:C(C)(=O)O;m3_m7:CN(C=O)C, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 60% sodium hydride in oil (0.24 g) was added to a solution of 5-(4-hydroxybenzylidene)-2,4-thiazolidinedione (0.664 g) in N,N-dimethylformamide (20 ml), and the mixture was stirred for 30 minutes. A solution of 4-chloromethyl-5-methyl-2-phenyloxazole (0.623 g) in N,N-dimethylformamide (10 ml) was added dropwise to the mixture under ice-cooling. After stirring at room temperature for 5 hours, the reaction solution was poured into water. The aqueous mixture was made acid with acetic acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was chromatographed on a column of silica gel (50 g). From the fractions eluted with ethyl acetatehexane (1:2, V/V), there was obtained 5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylidene]-2,4-thiazolidinedione (0.49 g, 40.8%). Recrystallization from chloroform-methanol afforded colorless prisms, m.p. 225°-226° C. Elemental analysis for C21H16N2O4S, Calcd.: C, 64.27; H, 4.11; N, 7.14. Found: C, 64.49; H, 3.96; H, 6.86. |
Here is a chemical reaction formula: Reactants are:m3_m7:BrCC(=O)C=1N=C(OC1C)C1=CC=CC=C1;m4:C(C)(=O)O;m1_m5_m2_m6:[H-].[Na+];m1_m5_m2_m6:OC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1, Reagents are:m3_m7:CN(C=O)C;m1_m5_m2_m6:CN(C=O)C, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)C(COC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 60% sodium hydride in oil (0.24 g) was added to a solution of 5-(4-hydroxybenzylidene)-2,4-thiazolidinedione (0.663 g) in N,N-dimethylformamide (20 ml) and the mixture was stirred for 30 minutes. Then, a solution of 4-bromoacetyl-5-methyl-2-phenyloxazole (0.841 g) in N,N-dimethylformamide (10 ml) was added dropwise to the mixture under ice-cooling. After stirring under ice-cooling for 30 minutes, the reaction solution was poured into ice-cold water. The aqueous mixture was made acid with acetic acid. The solid which precipitated was collected by filtration, washed with water, and crystallized from acetone to give 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione (0.42 g, 32.3%). Recrystallization from chloroform-ethanol yielded colorless needles, m.p. 244°-245° C. Elemental analysis for C22H16N2O5S, Calcd.: C, 62.85; H, 3.84; N, 6.66. Found: C, 62.80; H, 3.69; N, 6.93. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2:CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1;m1_m4_m2:C(C)(=O)O;m3_m5:CO, Reagents are:m1_m4_m2:[Pd];m3_m5:C(Cl)(Cl)Cl, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred mixture of 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione (500 mg), 10% Pd-C (50% wet, 1.0 g) and acetic acid (50 ml) was hydrogenated at 70° C. and at atmospheric pressure for 3 hours. Methanol (20 ml) and chloroform (20 ml) were added to the mixture and the whole was heated at 60° C. for 5 minutes. The mixture was filtered hot and the filtrate was concentrated in vacuo. A solution of the residue in ethyl acetate was successively washed with saturated aqueous sodium bicarbonate solution and water, and dried over magnesium sulfate. The solvent was removed and the residue was recrystallized from ethanol to yield 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-2,4-thiazolidinedione (the same compound as that obtained in Example 12) as crystals (415 mg, 82.7%). m.p. 113°-114° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:CC1=C(N=C(O1)C1=CC=CC=C1)C(COC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1)=O, Reagents are:m1_m2_m4:[Pd];m1_m2_m4:O1CCOCC1;m3:[Pd], and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)C(COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred mixture of 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione (1.0 g), Pd-black (3 g) and dioxane (100 ml) was hydrogenated at 40° C. and at atmospheric pressure. After 4 hours, another Pd-black (3 g) was added and hydrogenation was continued for 4 hours. The catalyst was filtered off and the filtrate was concentrated to yield 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzyl}-2,4-thiazolidinedione (the same compound as that obtained in Example 48) as crystals (0.95 g, 94.1%). Recrystallization from ethyl acetate-hexane gave colorless needles, m.p. 168°-169° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(CCC)(=O)N;m1_m2:ClCC(=O)CCl;m3:C([O-])(O)=O.[Na+], Reagents are:m4:O, and Products are 0:ClCC=1N=C(OC1)CCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of butyramide (19.88 g) and 1.3-dichloroacetone (24.14 g) was heated at 130° C. for 1.5 hours. After cooling, the mixture was diluted with water, neutralized with aqueous sodium bicarbonate solution and extracted with ethyl ether. The extract was washed with water, dried (MgSO4) and concentrated. The residue was purified by chromatography on silica gel with acetone-hexane (1:9) to yield 4-chloromethyl-2-propyloxazole as an oil (10.70 g 35.3%). NMR (CDCl3)δ: 0.97 (3H, t, J=7.5 Hz), 1.79 (2H, sext, J=7.5 Hz), 2.72 (2H, t, J=7.5 Hz), 4.47 (2H, s), 7.53 (1H, s). |
Here is a chemical reaction formula: Reactants are:m3:C([O-])(O)=O.[Na+];m1_m2:C(C1=CC=CC=C1)(=O)N;m1_m2:ClCC(CC(=O)OCC)=O, Reagents are:, and Products are 0:C1(=CC=CC=C1)C=1OC=C(N1)CC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of benzamide (60.0 g) and ethyl 4-chloroacetoacetate (49.4 g) was heated at 120° C. for 2 hours. After cooling, aqueous sodium bicarbonate solution was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated. The residue was purified by chromatography on silica gel with ethyl ether-hexane (1:9) to yield ethyl 2-phenyl-4-oxazoleacetate as an oil (26.4 g, 28.0%). NMR (CDCl3)δ: 1.27 (3H, t, J=7 Hz), 3.68 (3H, s), 4.15 (2H, q, J=7 Hz), 7.4 (3H, m), 7.67 (1H, s), 8.0 (2H, m). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C1(CCCCC1)C(N)=S;m1_m2_m3:ClCC(CC(=O)OCC)=O, Reagents are:m1_m2_m3:C(C)O, and Products are 0:C1(CCCCC1)C=1SC=C(N1)CC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of cyclohexanethiocarboxamide (5.0 g), ethyl 4-chloroacetoacetate (5.74 g), ethanol (50 ml) was heated under reflux for 1 hour. After dilution with water, mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium bicarbonate solution and water, dried (MgSO4), and concentrated. The residue was purified by chromatography on silica gel with ethyl acetate-hexane (1:4) to yield ethyl 2-cyclohexyl-4-thiazoleacetate as an oil (6.3 g, 70.9%). IR (Neat): 1735, 1255 cm-1. NMR (CDCl3)δ: 1.28 (3H, t, J=7 Hz), 1.2-2.3 (10H, m), 2.97 (1H, m), 3.77 (2H, s), 4.17 (2H, q, J=7 Hz), 7.0 (1H, s). |
Here is a chemical reaction formula: Reactants are:m2_m6:[H-].[Al+3].[Li+].[H-].[H-].[H-];m1_m5:CC1=C(N=C(O1)C1=CC=CC=C1)CC(=O)OC;m3:C(C)(=O)OCC;m4:O, Reagents are:m2_m6:C(C)OCC;m1_m5:C(C)OCC, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)CCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of methyl 5-methyl-2-phenyl-4-oxazoleacetate (54 g) in dry ethyl ether (150 ml) was added dropwise to a stirred, ice-cooled suspension of lithium aluminum hydride (8.8 g) in dry ethyl ether (700 ml) during 1.5 hours. Ethyl acetate (20 ml) was added dropwise thereto with ice-cooling and then water (50 ml) was added cautiously thereto. The resulting white precipitate was filtered off and the filtrate was concentrated to give 2-(5-methyl-2-phenyl-4-oxazolyl) ethanol as crystals (45.8 g, 96.2%). Recrystallization from ethyl acetate-hexane gave colorless rods, m.p. 73°-74° C. |
Here is a chemical reaction formula: Reactants are:m4:O;m3_m6:[H-].[Na+];m1_m2_m5:CC=1OC(=C(N1)CCO)C;m1_m2_m5:FC1=CC=C(C=C1)[N+](=O)[O-], Reagents are:m1_m2_m5:CN(C=O)C, and Products are 0:CC=1OC(=C(N1)CCOC1=CC=C(C=C1)[N+](=O)[O-])C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2-(2,5-Dimethyl-4-oxazolyl)ethanol (17.0 g) and 4-fluoronitrobenzene (17.0 g) were dissolved in N,N-dimethylformamide (150 ml), and 60% sodium hydride in oil (6.0 g) was added dropwise to the solution under vigorous stirring. After stirring at room temperature for 1 hour, the reaction mixture was poured into water (1 l) and the crystals which separated out were collected by filtration and recrystallized from ethyl acetate-hexane to give 4-[2-(2,5-dimethyl-4-oxazolyl)ethoxy]nitrobenzene (27.5 g. 87.0%). Colorless columns, m.p. 97°-98° C. Elemental analysis for C13H14N2O4, Calcd.: C, 59.94; H, 5.38; N, 10.68. Found: C, 59.72; H, 5.44; N, 10.63. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m5:C(C)(=O)C=1N=C(OC1C)C1=CC=CC=C1;m1_m4_m2_m5:BrBr;m3:C([O-])(O)=O.[Na+], Reagents are:m1_m4_m2_m5:C(Cl)(Cl)Cl;m1_m4_m2_m5:C(Cl)(Cl)Cl, and Products are 0:BrCC(=O)C=1N=C(OC1C)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-acetyl-5-methyl-2-phenyloxazole (12.0 g) in chloroform (100 ml) was added at 50° C. a solution of bromine (10.5 g) in chloroform (10 ml). The mixture was further heated at 55° C. for 30 minutes and poured into saturated aqueous sodium bicarbonate solution (500 ml). The chloroform layer was separated and the aqueous layer was extracted with chloroform. The conbined chloroform layer was washed with water and dried (MgSO4). Evaporation of the solvent gave 4-bromoacetyl-5-methyl-2-phenyloxazole as crystals (14.5 g, 86.3%). Recrystallization from ethyl ether-hexane gave colorless rods, mp 88°-89° C. |
Here is a chemical reaction formula: Reactants are:m1:C(C1=CC=CC=C1)OC1=CC=C(C=C1)C=1OC(=C(N1)CCOC1=CC=C(C=C1)[N+](=O)[O-])C, Reagents are:m2:CO;m3:[Pd], and Products are 0:OC1=CC=C(C=C1)C=1OC(=C(N1)CCOC1=CC=C(N)C=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 4-{2-[2-(4-benzyloxyphenyl)-5-methyl-4-oxazolyl]ethoxy}nitrobenzene (10.65 g) in methanol (200 ml) was subjected to a catalytic hydrogenation over 10% Pd-C (50% wet, 4.0 g). After the catalyst was filtered off, the filtrate was concentrated to give 4-{2-[2-(4-hydroxyphenyl)-5-methyl-4-oxazolyl]ethoxy}aniline (6.21 g, 78.2%). Recrystallization from methanol afforded brownish prisms, m.p. 184°-185° C. Elemental analysis for C18H18N2O3 ; Calcd.: C, 69.66; H, 5.85; N, 9.03. Found: C, 69.69; H, 5.87; N, 9.01. |
Here is a chemical reaction formula: Reactants are:m1_m2:CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(\C=C/2\C(NC(S2)=O)=O)C=C1, Reagents are:m1_m2:C(C)#N, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(\C=C\2/C(NC(S2)=O)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of (Z)-5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione (200 mg) in acetonitrile (750 ml), in a quartz tube under a stream of nitrogen, was irradiated by a 300 W high-pressure mercury lamp for 3 hours. The solvent was distilled off, and the resulting crystals were chromatographed on a column of silica gel (200 g). Elution with hexane-ethyl acetate (1:1, V/V) gave (E)-5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione (40 mg, 20.0%). Recrystallization from dichloromethaneethanol yielded colorless needles, m.p. 216°-217° C. Elemental analysis for C22H18N2O4S; Calcd.: C, 65.01; H, 4.46; N, 6.89. Found: C, 64.69; H, 4.26; N, 7.11. The subsequent elution with hexane-ethyl acetate (1:1, V/v) allowed the recovery of (Z)-5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione (138 mg, 69.0%). |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C#N)C=C1;m1_m3_m2:C(=O)O, Reagents are:m1_m3_m2:[Ni], and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=CC=C(C=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzonitrile (6.5 g), Raney nickel alloy (6.5 g) and 70% formic acid (100 ml) was heated under reflux for 2 hours. The insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The remaining oily material was chromatographed on a column of silica gel, and from the fractions eluted with chloroform-hexane (1:1, V/V), there were obtained crystlas (5.2 g, 78.5%) of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde. Recrystallization from ether-hexane yielded colorless needles, m.p. 82°-84° C. Elemental analysis for C19H17NO3 ; Calcd.: C, 74.25; H, 5.57; N, 4.56. Found: C, 74.47; H, 5.53; N, 4.34. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:ClCC=1N=C(OC1C)C1=CC=CC=C1;m1_m2_m3:OC1=CC=C(C=O)C=C1;m1_m2_m3:C([O-])([O-])=O.[K+].[K+], Reagents are:, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC=C(C=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4-chloromethyl-5-methyl-2-phenyloxazole (3.12 g), 4-hydroxybenzaldehyde (1.83 g), potassium carbonate (2.28 g) and dimethylformaide (40 ml) was stirred under heating at 110° C. for 1 hour. The reaction solution was poured into ice-cold water, and the crystals which separated out were collected by filtration to give 4-(5-methyl-2-phenyl-4-oxazolyl)methoxybenzaldehyde (4.40 g, 99.8%). Recrystallization from ether-hexane yielded colorless prisms, m.p. 112°-113° C. Elemental analysis for C18H15NO3 ; Calcd.: C, 73.71; H, 5.15; N, 4.87. Found: C, 73.87; H, 5.26; N, 4.81. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:BrCC(=O)C=1N=C(OC1C)C1=CC=CC=C1;m1_m2_m3_m4:C(#N)C1=CC=C(C=C1)O;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], Reagents are:m1_m2_m3_m4:C(C)C(=O)C, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)C(COC1=CC=C(C#N)C=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4-bromoacetyl-5-methyl-2-phenyloxazole (7.0 g), p-cyanophenol (3.0 g), potassium carbonate (6.9 g) and methyl ethyl ketone (100 ml) was heated under reflux for 2 hours. The reaction mixture was concentrated under reduced pressure, and water (100 ml)-ether (100 ml) was added to the residue. The mixture was stirred, and the crystals were collected by filtration. Recrystallization from chloroform-ethanol afforded 4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzonitrile (6.3 g, 78.8%), as brownish prisms, m.p. 202°-203° C. |
Here is a chemical reaction formula: Reactants are:m4:O;m1_m2_m5_m3:[BH4-].[Na+];m1_m2_m5_m3:CC1=C(N=C(O1)C1=CC=CC=C1)C(COC1=CC=C(C#N)C=C1)=O;m1_m2_m5_m3:CN(C=O)C, Reagents are:m1_m2_m5_m3:CO, and Products are 0:OC(COC1=CC=C(C#N)C=C1)C=1N=C(OC1)C1=CC=CC(=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Sodium borohydride (0.654 mg) was added to a suspension of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzonitrile (5.5 g) in methanol (100 ml)-N,N-dimethylformamide (50 ml), followed by stirring at room temperature for 1 hour. The reaction solution was poured into water and the crystals which separated out were collected by filtration to give 4-[2-hydroxy-2-(5-methyl-phenyl-4-oxazolyl)ethoxy]benzonitrile (5.1 g, 92.7%). Recrystallization from acetone afforded colorless neddles, m.p. 176°-177° C. |
Here is a chemical reaction formula: Reactants are:m3:C(C)(=O)Cl;m4:Cl;m1_m5_m2:OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=S)OCC)\C)OC)C)=O;m1_m5_m2:N1=CC=CC=C1, Reagents are:m1_m5_m2:C(C)#N, and Products are 0:C(C)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=S)OCC)\C)OC)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1.6 g of ethyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-thiohexenoate in 120 ml of acetonitrile at 0° C. was added 0.74 ml of pyridine followed by 1.0 ml of acetyl chloride. After stirring for 2 hours the reaction mixture was poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic solution was dried over anhydrous magnesium sulfate and evaporated to an oil, which was triturated with ether to give ethyl (E)-6-(1,3-dihydro-4-acetoxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-thiohexenoate, m.p. 81°-84° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:ClC[Si](OC)(OC)OC;m1_m2:N, Reagents are:, and Products are 0:CO[Si](OC)(OC)CNC[Si](OC)(OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Chloromethyltrimethoxysilane (50.0 g., 0.29 mole) and ammonia (98.6 g., 5.80 mole) were charged to a 300 ml. stainless steel pressure vessel. The mixture was heated to 100° C. at 800 psi pressure for 8 hours and then cooled. The mixture was filtered. The crude product was distilled at 60° C. and 0.2 mm Hg pressure to produce N,N-bis-(trimethoxysilylmethyl)amine. The N,N-bis-(trimethoxysilylmethyl)amine so produced (3.0 g., 0.01 mole) was found to be greater than 95% pure by gas chromatography. |
Here is a chemical reaction formula: Reactants are:m1:N([C@@H](C)C(=O)N[C@H](CCC(O)=O)C(=O)OC)C(=O)OC(C)(C)C;m2:C[Si](C)(C)C(C(=O)N)[Si](C)(C)C;m3:C(CCCCCCCCCCCCCCCCC)(=O)Cl;m4:O, Reagents are:m5:C(Cl)Cl, and Products are 0:N([C@@H](C)C(=O)N[C@H](CCC(O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: L-Ala-D-Glu(OH)OBzl (1) (942 mg) was suspended in methylene chloride (40 ml), and bis(trimethylsilyl)acetamide (1.20 g) was added to the suspension under stirring. The resulting solution was treated with stearoyl chloride (900 mg) at ambient temperature and left for an hour. Evaporation of the solvent gave an oily residual which was treated with water to give white solides. The solides were collected by filtration, washed with water and dried over magnesium sulfate to give stearoyl-L-Ala-D-Glu(OH)OBzl (2) (1.60 g). |
Here is a chemical reaction formula: Reactants are:m6_m8_m4:C(C)(=O)OCC;m6_m8_m4:CC(=O)C;m3_m5:C(C1=CC=CC=C1)OC(=O)ON=C(C#N)C1=CC=CC=C1;m3_m5:CC(=O)C;m1_m7_m2:N([C@@H](C)C(=O)N[C@H](CCC(O)=O)C(=O)OC)C(=O)OC(C)(C)C;m1_m7_m2:C(C)N(CC)CC, Reagents are:m6_m8_m4:O;m1_m7_m2:O, and Products are 0:N([C@@H](C)C(=O)N[C@H](CCC(O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of D-Lac-L-Ala-γ-D-Glu(α-OH)-(L)-mesoDAP-(L)-GlyOH (1) (1.2 g) in water (5 ml) was added triethylamine (0.96 g) and a solution of benzyloxycarbonyloxyimino-2-phenylacetonitrile (0.69 g) in acetone (5 ml) at 0° C. with stirring and the mixture was stirring over night at room temperature. After evapolation of acetone to the residue was added water (5 ml) and ethyl acetate (5 ml). The aqueous layer was separated, washed with ethyl acetate (5 ml), acidified with 1N-hydrochloric acid, and extracted with ethyl acetate (20 ml). The extract was washed with water (5 ml×2) and dried over magnesium sulfate. Evaporation of the solvent gave 1.42 g (94.7%) of D-Lac-L-Ala-γ-D-Glu(α-OH)-(L)-Z-(D)-mesoDAP-(L)-GlyOH (2). ##STR551## |
Here is a chemical reaction formula: Reactants are:m1_m4_m5:N([C@@H](C)C(=O)N[C@H](CCC(O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCC;m2_m3:ON1C(CCC1=O)=O;m2_m3:C1(CCCCC1)N=C=NC1CCCCC1, Reagents are:m1_m4_m5:O1CCCC1;m1_m4_m5:C(Cl)(Cl)Cl, and Products are 0:N([C@@H](C)C(=O)N[C@H](CCC(ON1C(=O)CCC1=O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of palmitoyl-L-Ala-D-Glu(OH)OBzl (1)(1.84 g) in a mixture of tetrahydrofuran (20 ml) and chloroform (30 ml) were added N-hydroxysuccinimide (425 mg) and dicyclohexylcarbodiimide (728 mg). The reaction mixture was kept for 18 hours at room temperature and the precipitate was filtered off and washed with chloroform. The filtrate was concentrated in vacuo and the diisopropylether was added to the residue. The product was collected and dried to afford palmitoyl-L-Ala-D-Glu(OSu)OBzl (2)(170 g). |
Here is a chemical reaction formula: Reactants are:m1_m2:FC(C(=O)O)(F)F;m1_m2:N([C@@H](C)C(=O)N[C@H](CCC(O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCC, Reagents are:, and Products are 0:N([C@@H](C)C(=O)N[C@H](CCC(ON1C(=O)CCC1=O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Trifluoroacetic acid (15 ml) was added to Boc-L-Ala-D-Glu-(OH)OBzl (1)(3.26 g) and the mixture was stirred for 20 minutes at room temperature, concentrated in vacuo and washed with diisopropylether. The oil was dissolved in a mixture of water (15 ml) and sodium bicarbonate was added until the pH of the solution became 8-9. The mixture of water (6 ml) and acetone (20 ml) was added to the solution and palmitoyl chloride (2.20 g) was added in one portion. After stirring for 30 minutes at room temperature, the pH of the solution was adjusted to 3 with 1N-hydrochloric acid and the reaction mixture was concentrated. To the residue was added water (30 ml) and the precipitates was collected and dried to give a crude product, which was purified by column chromatography of Silicagel (90 g) with chloroform-methanol (30:1, v/v) as an eluent to give palmitoyl-L-Ala-D-Glu(OH)OBzl (2)(2.00 g). mp. 131°-132° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m6:C(OC(C)Cl)(OCC1=CC=CO1)=O;m1_m2_m5_m6:NCC(=O)OCC;m3_m4:O;m3_m4:[Na+].[Cl-], Reagents are:m1_m2_m5_m6:C1CCOC1;m1_m2_m5_m6:C([O-])([O-])=O.[K+].[K+], and Products are 0:C(C1=CC=CO1)OC(=O)NCC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2.05 g (10 mmol) of α-chloroethyl furfuryl carbonate are added to a solution of 1.03 g (10 mmol) of ethyl glycinate in 6 ml of THF and 4 ml of 0.5M potassium carbonate solution maintained at between 5° and 10° C. The mixture is allowed to come to room temperature and is stirred for 18 hours. 50 ml of water saturated with NaCl are added and the mixture is extracted with 3×40 ml of ethyl ether. The organic phases are combined and dried over magnesium sulphate. After removal of the solvent and distillation, 1.5 g (66% yield) of the expected product is collected. |
Here is a chemical reaction formula: Reactants are:m1_m3_m4:C(SCCOCC)([S-])=S.[K+];m2_m5:C(C)SC1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])Cl)=O, Reagents are:m1_m3_m4:[Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC;m1_m3_m4:C(Cl)Cl;m2_m5:C(Cl)Cl, and Products are 0:C(C)SC1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])SC(=S)SCCOCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 3.58 g potassium 2-ethoxyethyl trithiocarbonate and 3.7 g benzyltriethylammonium chloride in 100 ml methylene chloride was cooled to 0° C. under a nitrogen atmosphere and a solution of 5.3 g of p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate in 50 ml methylene chloride was added dropwise. The reaction mixture was stirred for 1 hour, then washed with three 50 ml portions of water, dried over anhydrous sodium sulfate and concentrated in vacuo to an oil. (8.6 g). The crude product was chromatographed on silica gel eluting with 5% ethyl acetate in chloroform to yield 2.3 g of the title compound as an oil. The IR spectrum of a chloroform solution of the title compound had an absorption at 5.65 micron; and the NMR spectrum in deuterochloroform showed peeks at 1.2(m, 6H); 2.34-3.77(c, 10H); 4.7,4.98(m, 1H); 5.26(s, 2H); 6.62, 6.86(s, 1H); 7.43(m, 2H); and 8.16(m, 2H). ppm. |
Here is a chemical reaction formula: Reactants are:m1_m4:CC(C)([O-])C.[K+];m3:C(=S)=S;m2:C(C)OCCS, Reagents are:m1_m4:O1CCCC1, and Products are 0:C(SCCOCC)([S-])=S.[K+], please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 6.79 g potassium t-butoxide in 300 ml of anhydrous tetrahydrofuran cooled to 0° C. under a nitrogen atmosphere was added 6.42 g of 2-mercaptoethyl ethyl ether. The resulting slurry was stirred at 25° C. for 1 hour, then 4.4 ml. of carbon disulfide was added dropwise at 0° C. The resulting solution was stirred at 25° C. for 30 min., then concentrated in vacuo. Diethyl ether (300 ml) was added and the mixture was filtered, washed with ether and dried under nitrogen to yield 12.6 g of the title compound as a yellow solid. |
Here is a chemical reaction formula: Reactants are:m4_m3:C(C)(=O)OC;m1_m5_m2:C(C)(=O)OCC=1C(=NC=C(N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O;m1_m5_m2:C1(=CC=C(C=C1)S(=O)(=O)O)C, Reagents are:m4_m3:CO;m1_m5_m2:CO, and Products are 0:ClC(C=1N=C(C(=NC1)N1C(C=2C(C1=O)=CC=CC2)=O)CO)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 15 g (0.04 mole) of 3-acetoxymethyl-5-dichloromethyl-2-phthalimidopyrazine, 150 ml of methanol and 0.15 g of p-toluenesulfonic acid was heated to the boil, and a mixture of methanol and methyl acetate was slowly distilled off in the course of 5 hours. The mixture was then evaporated down to one-third of its total volume, and the precipitated crystals were isolated, and recrystallized from ethyl acetate. 7.18 g (54%) of 5-dichloromethyl-3-hydroxymethyl-2-phthalimidopyrazine of melting point 188°-189° C. were obtained. 1H-NMR (CDCl3 270 MHz): δ4.7 (s, 2H), 6.9 (s, 1H), 8.1 (m, 4H), 9.1 (s, 1H). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1;m1_m2_m3:OCC=1C(=NC=C(N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O, Reagents are:m1_m2_m3:ClCCl, and Products are 0:C(=O)C=1C(=NC=C(N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5.1 g of pyridinium chlorochromate were added a little at a time to a solution of 4 g of 3-hydroxymethyl-5-dichloromethyl-2-phthalimidopyrazine in 80 ml of dichloromethane at 35° C., after which the mixture was stirred for 40 minutes and filtered over silica gel, and the filtrate was evaporated down. 3.1 g (76%) of colorless crystals of 3-formyl-5-dichloromethyl-2-phthalimidopyrazine of melting point 145°-146° C. (from ethyl acetate) were obtained. 1H-NMR (270 MHz, CDCl3): δ6.9 (s, 1H), 8.0 (m, 4H), 9.3 (s, 1H), 10.1 (s, 1H). |
Here is a chemical reaction formula: Reactants are:m1_m4:C(=O)C=1C(=NC=C(N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O;m2:Cl.NO;m3:O, Reagents are:m1_m4:CS(=O)C, and Products are 0:N(O)=C1C(N=CC(=N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 10 g of 3-formyl-5-dichloromethyl-2-phthalimidopyrazine in 50 ml of dimethyl sulfoxide was heated at 50° C., 7 g of hydroxylamine hydrochloride were added, and the mixture was stirred for 15 minutes at 70° C. Thereafter, 700 ml of water were added to the reaction solution, the mixture was filtered and the filtrate was washed with a little diethyl ether. 6.8 g of colorless crystals (65%) of 3-oximinodichloromethyl-2-phthalimidopyrazine were obtained. 1H-NMR (270 MHz, DMSO-d6): δ7.7 (s, 1H), 8.0 (m, 4H), 8.3 (s, 1HO), 9.1 (s, 1H), 12.0 (s, OH). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:O.NN;m1_m2_m3:C(#N)C=1C(=NC=C(N1)C(OC)OC)N1C(C=2C(C1=O)=CC=CC2)=O, Reagents are:m1_m2_m3:CO, and Products are 0:NC1=NC=C(N=C1C#N)C(OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.2 g of hydrazine hydrate were added dropwise to a suspension of 2 g of 3-cyano-5-dimethoxymethyl-2-phthalimidopyrazine in 40 ml of absolute methanol at 40° C. Immediately after the addition, the solution became clear, and crystals were precipitated after a few minutes. Chromatography over silica gel gave 0.9 g (75%) of 2-amino-3-cyano-5-dimethoxymethylpyrazine. 1H-NMR (270 MHz, DMSO-d6): δ3.3 (s, 6H), 5.0 (s, 1H), 8.35 (s, 1H). |
Here is a chemical reaction formula: Reactants are:m1:NC1=NC(=C(C=C1C#N)C#N)Cl, Reagents are:m2:C1CCCCC1.CCOC(=O)C, and Products are 0:NC1=NC=C(C=C1C#N)C#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2-Amino-3,5-dicyanopyridine (5) was prepared from 3 using the procedure described below for the preparation of 5 except that 5 was recrystallised from MeCN [methyl cyanide; acetonitrile) (instead of EtOH). The yield was 73% (7.00 g from 12.0 g (67.2 mmol) of 3] of product homogeneous on TLC (cyclohexane-EtOAc, 1:1); mp 220° C. dec; 1H NMR (Me2SO-d6) δ7.90 (s, NH2), 8.40 and 8.58 (two d, 4-H and 6H, J=2 Hz). |