Phosgene → N-ethyl-N-(oxan-4-yl)carbamoyl chloride

Participants

Reaction Steps

At −30° C., a solution of 19 g (0.15 mol) of ethyl(tetrahydro-2H-pyran-4-yl)amine and 14.8 g (0.15 mol) of triethylamine in 10 ml of dichloromethane was slowly added dropwise to a solution of 44 g (0.44 mol) of phosgene in 100 ml of dichloromethane. The mixture was slowly warmed to room temperature (over a period of approximately 3 hours) and then heated under reflux for 30 minutes, excess phosgene was removed using a nitrogen stream, and the solution was concentrated. 200 ml of hexane were added, the solids were filtered off and the filtrate was concentrated. Yield 25.3 g. MS (m/z): 192 [M+H]+, 156 [M−Cl]+.

Provenance & Evidence