Benzenesulfonamide → 1,1-Diphenylurea

Participants

Reaction Steps

6.5 g of sodium salt of 4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonamide were refluxed for 3 hours with 3.9 g of diphenylcarbamic acid chloride in 60 ml of toluene. The crude N-[4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonyl]-N',N'-diphenyl-urea obtained was suction-filtered, suspended in dioxane and, after addition of 1 g of acetic acid and 1.6 g of cyclopentyl-amine, the substance was refluxed for 11/2 hours. After acidification with dilute hydrochloric acid the precipitate was separated by suction-filtration and treated with 0.5 %-ammonia. The aqueous alkaline solution was acidified and the crystals were re-crystallized from methanol. N-[4-(β-<2-methoxy-5-chloro-benzamido>-ethyl)-benzenesulfonyl] -N'-cyclopentyl-urea was obtained having a melting point of 182° - 184°C.

Provenance & Evidence