Ethylamine → N-Ethyl 2-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionamide

Participants

Reaction Steps

A mixture of 70% aqueous ethylamine (0.46 g) and dichloromethane (5 ml) was cooled, with stirring, in an ice bath. A solution of the acid chloride (1.05 g; prepared as described in part (a) above) in dichloromethane (5 ml) was added and the mixture was stirred for 7 hours and then allowed to stand overnight. After this time thin layer chromatography indicated that the reaction had not gone to completion and therefore a further portion of 70% aqueous ethylamine was added and the mixture was heated under reflux for a period of 3 hours. The mixture was allowed to cool, made up to 30 ml with dichloromethane and was washed with water (4×20 ml). The organic phase was dried over anhydrous magnesium sulfate and the solvent removed by evaporation. The solid residue was purified by preparative thin layer chromatography on silica gel (eluent dichloromethane/isopropyl alcohol 20:1) to give the title compound (0.74 g), mp 141°-142° C. The pmr spectrum of the compound was consistent with the assigned structure.

Provenance & Evidence