Phosgene → N-methyl-N-[2-(trifluoromethyl)phenyl]carbamoyl chloride

Participants

Reaction Steps

A mixture of 1.00 g (5.71 mmole) of 2-(methylamino)benzotrifluoride, 9 mL (17.3 mmole) of 1.93M phosgene in toluene, and 10 mL of toluene was stirred under N2 for a hour and then treated with 20 mL of 2.5N sodium hydroxide (aqueous). The layers were separated, and the organic phase was concentrated in vacuo to yield 1.12 g (83%) of the title compound as a clear oil, which eventually solidified after prolonged standing: mp 44°-46° C.; homogeneous by TLC in 3:1 hexane-EtOAc; IR spectrum νCO 1750 cm-1 ; FAB-MS m/e 237 (M+1)+.

Provenance & Evidence