Ammonia → N-trimethylsilylbenzamide

Participants

Reaction Steps

6.4 ml of hexamethyldisilazane (31 mmoles) were added to a refluxing mixture of 15 ml of toluene, 40 mg of saccharin (0.22 mmole) and 5.0 g of benzamide (41.3 mmoles) and the ammonia liberated was led into water by a stream of nitrogen passed over the reaction mixture. Titration with 1 N H2SO4 revealed that the calculated amount of ammonia was evolved in 15 minutes and solvent and excess hexamethyldisilazane were evaporated in vacuo to obtain 8.04 g (101%) of N-trimethylsilylbenzamide melting at 111°-115° C. The experiment was repeated without the addition of saccharin and it was found that 82% of the theoretical amount of ammonia was evolved in 15 minutes and 88% of it in 50 minutes.

Provenance & Evidence