2-chloro-N,N-dimethylbenzenesulfonamide

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: To a stirred mixture of 29 g of 2-chloro-N,N-dimethylbenzenesulfonamide and 150 mL ether at -5° C. to 0° C. was added dropwise under nitrogen 94 mL of a 1.55M solution of n-butyllithium in hexanes. When the addition was complete, the reaction mixture was allowed to warm to room temperature and was stirred for 2 hours. The reaction mixture was then recooled to -30° C. to -20° C., and treated with a solution of 22 mL of sulfuryl chloride in 60 mL hexanes, added at a rate that maintained the temperature below -10° C. The reaction mixture was then stirred at room temperature for one hour. The precipitated solids were collected, washed with ether and water, and dried to afford 26 g of 3-chloro-2-(N,N-dimethylsulfamoyl)benzenesulfonyl chloride as a yellow solid, which was used without further purification; IR (KBr): 1375, 1350, 1180 and 1160 cm-1. When the addition was then recooled to -30° C. to -20° C. added at a rate that maintained the temperature below -10° C The reaction mixture was then stirred at room temperature for one hour The precipitated solids were collected washed with ether and water dried

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

実験手順: A stirred solution of 63.3 g of 2-chlorobenzensulfonyl chloride in 500 mL of tetrahydrofuran was cooled to 0°-5° C. and treated with 46 mL of dimethylamine, added dropwise at a rate that maintained the temperature below 10° C. The resulting mixture was allowed to warm gradually to room temperature. The precipitate was removed by filtration, and was washed well with tetrahydrofuran. The combined filtrates were evaporated in vacuo and the resulting oil was dissolved in 400 mL of methylene chloride, washed with two 200-mL portions of water, and dried over MgSO4. Evaporation of the solvent in vacuo afforded an oil, which solidified upon standing. Trituration with hexanes afforded 58.6 g of 2-chloro-N,N-dimethylbenzenesulfonamide as a white solid, m.p. 49°-51° C.; NMR (CDCl3): δ2.9 (s, 6H), 7.3-7.7 and 7.9-8.2 (m, 4H); IR(KBr): 1340 and 1170 cm-1. added dropwise at a rate that maintained the temperature below 10° C The precipitate was removed by filtration was washed well with tetrahydrofuran The combined filtrates were evaporated in vacuo the resulting oil was dissolved in 400 mL of methylene chloride washed with two 200-mL portions of water dried over MgSO4 Evaporation of the solvent in vacuo afforded an oil, which

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

実験手順: To a stirred mixture of 29 g of 2-chloro-N,N-dimethylbenzenesulfonamide and 150 mL ether at -5° C. to 0° C. was added dropwise under nitrogen 94 mL of a 1.55M solution of n-butyllithium in hexanes. When the addition was complete, the reaction mixture was allowed to warm to room temperature and was stirred for 2 hours. The reaction mixture was then recooled to -30° C. to -20° C., and treated with a solution of 22 mL of sulfuryl chloride in 60 mL hexanes, added at a rate that maintained the temperature below -10° C. The reaction mixture was then stirred at room temperature for one hour. The precipitated solids were collected, washed with ether and water, and dried to afford 26 g of 3-chloro-2-(N,N-dimethylsulfamoyl)benzenesulfonyl chloride as a yellow solid, which was used without further purification; IR (KBr): 1375, 1350, 1180 and 1160 cm-1. When the addition was then recooled to -30° C. to -20° C. added at a rate that maintained the temperature below -10° C The reaction mixture was then stirred at room temperature for one hour The precipitated solids were collected washed with ether and water dried

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

実験手順: A stirred solution of 63.3 g of 2-chlorobenzensulfonyl chloride in 500 mL of tetrahydrofuran was cooled to 0°-5° C. and treated with 46 mL of dimethylamine, added dropwise at a rate that maintained the temperature below 10° C. The resulting mixture was allowed to warm gradually to room temperature. The precipitate was removed by filtration, and was washed well with tetrahydrofuran. The combined filtrates were evaporated in vacuo and the resulting oil was dissolved in 400 mL of methylene chloride, washed with two 200-mL portions of water, and dried over MgSO4. Evaporation of the solvent in vacuo afforded an oil, which solidified upon standing. Trituration with hexanes afforded 58.6 g of 2-chloro-N,N-dimethylbenzenesulfonamide as a white solid, m.p. 49°-51° C.; NMR (CDCl3): δ2.9 (s, 6H), 7.3-7.7 and 7.9-8.2 (m, 4H); IR(KBr): 1340 and 1170 cm-1. added dropwise at a rate that maintained the temperature below 10° C The precipitate was removed by filtration was washed well with tetrahydrofuran The combined filtrates were evaporated in vacuo the resulting oil was dissolved in 400 mL of methylene chloride washed with two 200-mL portions of water dried over MgSO4 Evaporation of the solvent in vacuo afforded an oil, which

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: To a stirred mixture of 29 g of 2-chloro-N,N-dimethylbenzenesulfonamide and 150 mL ether at -5° C. to 0° C. was added dropwise under nitrogen 94 mL of a 1.55M solution of n-butyllithium in hexanes. When the addition was complete, the reaction mixture was allowed to warm to room temperature and was stirred for 2 hours. The reaction mixture was then recooled to -30° C. to -20° C., and treated with a solution of 22 mL of sulfuryl chloride in 60 mL hexanes, added at a rate that maintained the temperature below -10° C. The reaction mixture was then stirred at room temperature for one hour. The precipitated solids were collected, washed with ether and water, and dried to afford 26 g of 3-chloro-2-(N,N-dimethylsulfamoyl)benzenesulfonyl chloride as a yellow solid, which was used without further purification; IR (KBr): 1375, 1350, 1180 and 1160 cm-1. When the addition was then recooled to -30° C. to -20° C. added at a rate that maintained the temperature below -10° C The reaction mixture was then stirred at room temperature for one hour The precipitated solids were collected washed with ether and water dried

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

実験手順: A stirred solution of 63.3 g of 2-chlorobenzensulfonyl chloride in 500 mL of tetrahydrofuran was cooled to 0°-5° C. and treated with 46 mL of dimethylamine, added dropwise at a rate that maintained the temperature below 10° C. The resulting mixture was allowed to warm gradually to room temperature. The precipitate was removed by filtration, and was washed well with tetrahydrofuran. The combined filtrates were evaporated in vacuo and the resulting oil was dissolved in 400 mL of methylene chloride, washed with two 200-mL portions of water, and dried over MgSO4. Evaporation of the solvent in vacuo afforded an oil, which solidified upon standing. Trituration with hexanes afforded 58.6 g of 2-chloro-N,N-dimethylbenzenesulfonamide as a white solid, m.p. 49°-51° C.; NMR (CDCl3): δ2.9 (s, 6H), 7.3-7.7 and 7.9-8.2 (m, 4H); IR(KBr): 1340 and 1170 cm-1. added dropwise at a rate that maintained the temperature below 10° C The precipitate was removed by filtration was washed well with tetrahydrofuran The combined filtrates were evaporated in vacuo the resulting oil was dissolved in 400 mL of methylene chloride washed with two 200-mL portions of water dried over MgSO4 Evaporation of the solvent in vacuo afforded an oil, which