m-Chloroperbenzoic acid → HCID 14183130, compound

Participants

Reaction Steps

A solution of 23.9 g of 85% m-chloroperoxybenzoic acid in 125 ml of 1,2-dimethoxyethane (DME hereafter) was added dropwise over 1 hour to a solution of 14 g of 3-(4-methoxyphenyl)-1,2,4-thiadiazole-5-sulfenamide in 300 ml of DME at -5° (ice/methanol bath). The resulting solution was stirred at room temperature overnight. Concentration gave a solid mass which was stirred for 2 hours with 300 ml of saturated sodium bicarbonate solution, collected, washed with water and dried to give 14.8 g of crude product. Flash chromatography using a step gradient of 12 to 15% ethyl acetate/dichloromethane gave 1.37 g of solid, m.p. 144°-147°.

Provenance & Evidence