Ammonia → 2,5-Pyrrolidinedione, 1-(trimethylsilyl)-

Participants

Reaction Steps

15.6 ml (0.075 mole) of hexamethyldisilazane were added dropwise over a few minutes to a refluxing suspension of 9.90 g (0.1 mole) of succinimide and 0.24 g (0.5 mmole) of di-4-nitrophenyl N-4-toluenesulfonyl-phosphoramidate in 50 ml of dichloromethane and a stream of nitrogen was led over the reaction mixture to pass the ammonia evolved into water. The progress of the reaction was established by titration of the ammonia evolved and it was found that after refluxing for 1.5 hours, the production of ammonia was completed. 90% of the theoretical amount of ammonia had been evolved and refluxing was continued for another 2 hours. Then the solvent was removed by distillation at normal pressure and fractionation under reduced pressure yielded 15.36 g (89.8%) of N-trimethylsilylsuccinimide boiling at 118°-119° C. at 18 mm Hg and nD 25=1.4745.

Provenance & Evidence