Thiophosgene → N-[3-[(7,8-Didehydro-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl)oxy]propoxy]-4-isothiocyanatobenzamide

Participants

Reaction Steps

A stirred solution of 0.5 g (1.1 mmol) of N-[3-[(7,8-Didehydro-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl)oxy]propoxy]-4-aminobenzamide in 10 ml of methylene chloride was treated with 0.5 g of solid anhydrous sodium bicarbonate followed by 150 ul (1.9 mmol) of thiophosgene and stirred at room temperature for 30 minutes. The solvent was removed in vacuo and the residue was chromatographed on 150 g of silica gel using 15% methanol-chloroform to give 230 mg of N-[3-[(7,8-Didehydro-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl)oxy]propoxy]-4-isothiocyanatobenzamide as an amorphous solid.

Provenance & Evidence