methyl 2-(sulfamoylmethyl)benzoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1.9 g of (4,6-dimethoxypyrimidin-2-yl)acetic acid in 40 ml of absolute dichloromethane is added dropwise at 0° C. to 2° C. to a solution of 1.9 g of dicyclohexylcarbodiimide, 100 mg of 4-dimethylaminopyridine and 2.1 g of 2-methoxycarbonylbenzylsulfonamide in 40 ml of absolute dichloromethane. Stirring is continued for 1 hour at 0° C., and the mixture is allowed to come to room temperature and stirred for another 0.5 hour. The solids are filtered off, and the filtrate is concentrated in a rotary evaporator. 100 ml of 2 N sodium carbonate solution are added to the residue, the mixture is stirred for 0.5 hour at room temperature, and the solids are filtered off with suction. The sodium carbonate alkaline phase is extracted twice using diethyl ether, and a pH of 2-3 is established using concentrated hydrochloric acid. Stirring is continued for 15 minutes, the solids are filtered off with suction, the filter residue is washed once with water and twice with ether, and dried in vacuo. This gives 2.4 g of N-[2-(4,6-dimethoxypyrimidin-2-yl)acetyl]-2-methoxycarbonylbenzylsulfonamide of melting point 98°-101° C. to come to room temperature stirred for another 0.5 hour The solids are filtered off the filtrate is concentrated in a rotary evaporator 100 ml of 2 N sodium carbonate solution are added to the residue the mixture is stirred for 0.5 hour at room temperature the solids are filtered off with suction The sodium carbonate alkaline phase is extracted twice using diethyl ether Stirring is continued for 15 minutes the solids are filtered off with suction the filter residue is washed once with water and twice with ether dried in vacuo

反応条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2.5 g of (2-methoxycarbonylbenzyl)sulfonamide, 21.5 g of 4,6-dimethoxy-2-isothiocyanatopyrimidine and 15.1 g of anhydrous potassium carbonate in 400 ml of acetone is stirred for 8.5 hours at 55° C., and then filtered to collect precipitated crystals. To the filtrate, further 2 g of anhydrous potassium carbonate is added and stirred for 2 hours at 60° C. The precipitated crystals are collected. The combined crystals are suspended in 1.5 of water and adjusted to pH 2 with hydrochloric acid. After stirring the mixture for an hour, the crystals are collected by filtration, washed with water, dried and recrystallized from acetonitrile to give 35.9 g of the title compound, as white powder. filtered to collect precipitated crystals To the filtrate, further 2 g of anhydrous potassium carbonate is added stirred for 2 hours at 60° C The precipitated crystals are collected After stirring the mixture for an hour the crystals are collected by filtration washed with water dried recrystallized from acetonitrile

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 84 g of methyl 2-[(aminosulfonyl)methyl]benzoate in 300 ml of absolute ethanol was added dropwise 22 g of hydrazine monohydrate. The thick suspension was heated at reflux for about 16 hours to yield a solution, then a thick suspension, at reflux temperature. The suspension was cooled to 20° C. filtered, and the residue was washed 1×100 ml of water and suction dried about three hours to provide 49 g of the subject compound; m.p. 221°-222° C. The thick suspension was heated at reflux for about 16 hours to yield a solution a thick suspension, at reflux temperature filtered the residue was washed 1×100 ml of water and suction dried about three hours

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 84 g of methyl 2-[(aminosulfonyl)methyl]benzoate in 300 ml of absolute ethanol was added dropwise 22 g of hydrazine monohydrate. The thick suspension was heated at reflux for about 16 hours to yield a solution, then a thick suspension, at reflux temperature. The suspension was cooled to 20° C. filtered, and the residue was washed 1×100 ml of water and suction dried about three hours to provide 49 g of the subject compound; m.p. 221°-222° C. The thick suspension was heated at reflux for about 16 hours to yield a solution a thick suspension, at reflux temperature filtered the residue was washed 1×100 ml of water and suction dried about three hours

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 84 g of methyl 2-[(aminosulfonyl)methyl]benzoate in 300 ml of absolute ethanol was added dropwise 22 g of hydrazine monohydrate. The thick suspension was heated at reflux for about 16 hours to yield a solution, then a thick suspension, at reflux temperature. The suspension was cooled to 20° C., filtered, and the residue was washed 1×100 ml of water and suction dried about three hours to provide 49 g of the subject compound; m.p. 221°-222° C. The thick suspension was heated at reflux for about 16 hours to yield a solution a thick suspension, at reflux temperature filtered the residue was washed 1×100 ml of water and suction dried about three hours

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 84 g of methyl 2-[(aminosulfonyl)methyl]benzoate in 300 ml of absolute ethanol was added dropwise 22 g of hydrazine monohydrate. The thick suspension was heated at reflux for about 16 hours to yield a solution, then a thick suspension, at reflux temperature. The suspension was cooled to 20° C., filtered, and the residue was washed 1×100 ml of water and suction dried about three hours to provide 49 g of the subject compound; m.p. 221°-222° C. The thick suspension was heated at reflux for about 16 hours to yield a solution a thick suspension, at reflux temperature filtered the residue was washed 1×100 ml of water and suction dried about three hours

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1.9 g of (4,6-dimethoxypyrimidin-2-yl)acetic acid in 40 ml of absolute dichloromethane is added dropwise at 0° C. to 2° C. to a solution of 1.9 g of dicyclohexylcarbodiimide, 100 mg of 4-dimethylaminopyridine and 2.1 g of 2-methoxycarbonylbenzylsulfonamide in 40 ml of absolute dichloromethane. Stirring is continued for 1 hour at 0° C., and the mixture is allowed to come to room temperature and stirred for another 0.5 hour. The solids are filtered off, and the filtrate is concentrated in a rotary evaporator. 100 ml of 2 N sodium carbonate solution are added to the residue, the mixture is stirred for 0.5 hour at room temperature, and the solids are filtered off with suction. The sodium carbonate alkaline phase is extracted twice using diethyl ether, and a pH of 2-3 is established using concentrated hydrochloric acid. Stirring is continued for 15 minutes, the solids are filtered off with suction, the filter residue is washed once with water and twice with ether, and dried in vacuo. This gives 2.4 g of N-[2-(4,6-dimethoxypyrimidin-2-yl)acetyl]-2-methoxycarbonylbenzylsulfonamide of melting point 98°-101° C. to come to room temperature stirred for another 0.5 hour The solids are filtered off the filtrate is concentrated in a rotary evaporator 100 ml of 2 N sodium carbonate solution are added to the residue the mixture is stirred for 0.5 hour at room temperature the solids are filtered off with suction The sodium carbonate alkaline phase is extracted twice using diethyl ether Stirring is continued for 15 minutes the solids are filtered off with suction the filter residue is washed once with water and twice with ether dried in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1.9 g of (4,6-dimethoxypyrimidin-2-yl)acetic acid in 40 ml of absolute dichloromethane is added dropwise at 0° C. to 2° C. to a solution of 1.9 g of dicyclohexylcarbodiimide, 100 mg of 4-dimethylaminopyridine and 2.1 g of 2-methoxycarbonylbenzylsulfonamide in 40 ml of absolute dichloromethane. Stirring is continued for 1 hour at 0° C., and the mixture is allowed to come to room temperature and stirred for another 0.5 hour. The solids are filtered off, and the filtrate is concentrated in a rotary evaporator. 100 ml of 2 N sodium carbonate solution are added to the residue, the mixture is stirred for 0.5 hour at room temperature, and the solids are filtered off with suction. The sodium carbonate alkaline phase is extracted twice using diethyl ether, and a pH of 2-3 is established using concentrated hydrochloric acid. Stirring is continued for 15 minutes, the solids are filtered off with suction, the filter residue is washed once with water and twice with ether, and dried in vacuo. This gives 2.4 g of N-[2-(4,6-dimethoxypyrimidin-2-yl)acetyl]-2-methoxycarbonylbenzylsulfonamide of melting point 98°-101° C. to come to room temperature stirred for another 0.5 hour The solids are filtered off the filtrate is concentrated in a rotary evaporator 100 ml of 2 N sodium carbonate solution are added to the residue the mixture is stirred for 0.5 hour at room temperature the solids are filtered off with suction The sodium carbonate alkaline phase is extracted twice using diethyl ether Stirring is continued for 15 minutes the solids are filtered off with suction the filter residue is washed once with water and twice with ether dried in vacuo

反応条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2.5 g of (2-methoxycarbonylbenzyl)sulfonamide, 21.5 g of 4,6-dimethoxy-2-isothiocyanatopyrimidine and 15.1 g of anhydrous potassium carbonate in 400 ml of acetone is stirred for 8.5 hours at 55° C., and then filtered to collect precipitated crystals. To the filtrate, further 2 g of anhydrous potassium carbonate is added and stirred for 2 hours at 60° C. The precipitated crystals are collected. The combined crystals are suspended in 1.5 of water and adjusted to pH 2 with hydrochloric acid. After stirring the mixture for an hour, the crystals are collected by filtration, washed with water, dried and recrystallized from acetonitrile to give 35.9 g of the title compound, as white powder. filtered to collect precipitated crystals To the filtrate, further 2 g of anhydrous potassium carbonate is added stirred for 2 hours at 60° C The precipitated crystals are collected After stirring the mixture for an hour the crystals are collected by filtration washed with water dried recrystallized from acetonitrile