Dimethylamine → HCID 20215695, compound

Participants

Reaction Steps

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.

Provenance & Evidence