Ammonia → Methanesulfonamide, N-(trimethylsilyl)-

Participants

Reaction Steps

5.1 ml of hexamethyldisilazane (24.5 mmoles) were added to a refluxing mixture of 3.0 g (31.6 mmoles) of methanesulfonamide, 20 mg (0.11 mmole) of saccharin and 15 ml of toluene while a stream of nitrogen passed over the reaction mixture to expel the ammonia evolved, which was absorbed in water and titrated with 1 N H2SO4. It was found that after refluxing for 20 minutes the calculated amount of ammonia was evolved. The solvent and excess hexamethyldisilazane were evaporated in vacuo and the solid residue was vacuum dried to obtain 5.22 g (99.5%) of N-trimethylsilylmethanesulfonamide melting at 69°-74.5° C. The experiment was repeated without the addition of saccharin and the calculated amount of ammonia was evolved in 35 minutes. Workup as described above yielded 5.25 g (100%) of N-trimethylsilylmethansulfonamide melting at 68°-72.5° C.

Provenance & Evidence