Cyclohexylamine → 4-Chloro-N-cyclohexylbenzamide

Participants

Reaction Steps

Cyclohexylamine (80 gm., 0.8 mole) is dissolved in 2.5 l. of benzene and treated dropwise with 70 gm. (0.4 mole) of p-chlorobenzoyl chloride in 250 ml. of benzene over 45 minutes with intermittent cooling to maintain reaction temperature between 22°-30°. After stirring an additional 15 minutes, the mixture is diluted with benzene and washed with water. A suspended solid is filtered and the filtrate concentrated to 1 l. to give a second crop; these are combined and recrystallized from methanol, 65.0 gm. (68.5%), m.p. 191°-193°.

Provenance & Evidence