Triethylamine → N-(methanesulfonyloxy)-4-chlorobenzimidoyl chloride

Participants

Reaction Steps

A solution of 9.8 g of 4-chlorobenzohydroximoyl chloride in 300 ml of diethyl ether was chilled to 5°. To it was quickly added 10.4 g of triethylamine and, after 5 minutes, a solution of 6.1 g of methanesulfonyl chloride in 30 ml of diethyl ether was added dropwise during 30 minutes. The mixture was stirred for 1 hour at 0°-5°, followed by 1 hour at ambient temperature. The mixture was again cooled to 5°, then filtered, and the filter cake was washed with cold ether. The filtrate and washes were combined and the other evaporated under reduced pressure to leave a yellow oil. The oil was crystallized from a mixture of benzene and hexane to give 7.8 g of N-(methanesulfonyloxy)-4-chlorobenzimidoyl chloride, m.p. 80°-82°.

Provenance & Evidence