Phosgene → tert-Butyl(ethenyl)carbamyl chloride

Participants

Reaction Steps

60 parts of phosgene are introduced into 224 parts of methylene chloride. 39.6 parts of ethylidene-tert.-butylamine, 51 parts of dimethylcyclohexylamine and 210 parts of methylene chloride are added to this solution in the course of one hour at from 0° to 5° C., whilst stirring. The mixture is then stirred for 30 minutes, after which the reaction solution is freed from excess phosgene. The mixture is now thoroughly mixed with 250 parts of water at 0° C., whereupon the dimethylcyclohexylamine hydrochloride passes into the aqueous phase. This aqueous phase is separated off and neutralized with sodium hydroxide solution, and the dimethylcyclohexylamine is recovered by distillation. The organic phase is distilled. 52 parts of N-vinyl-N-tert.-butylcarbamoyl chloride (80% of theory) boiling at 85° C./14 mm Hg are obtained.

Provenance & Evidence