Methylamine → N-Methyl-o-toluenesulfonamide

Participants

Reaction Steps

To a solution of 2-methylbenzenesulfonyl chloride (37.4 g, 0.196 mol) in methylene chloride (300 ml) at -5° to 0° under nitrogen was added liquid methylamine (27.5 ml, 0.588 mol) at a rate to maintain an internal temperature less than 10°. The reaction mixture was stirred at 0° for 1/2 hour and then allowed to warm to room temperature. After 11/4 hours, filtration and concentration of the filtrate gave an oil which solidified upon cooling. Washing the solid with n-butyl chloride gave N,2-dimethylbenzenesulfonamide as a light yellow powder (28.4 g, 78%), mp. 62°-64°.

Provenance & Evidence