Tetrahydrofuran → 2-Oxocyclohexane-1-sulfonamide

Participants

Reaction Steps

A solution of 16.7 g (0.1 mol) of morpholinocyclohexene in 200 ml of tetrahydrofuran was treated simultaneously, over a period of 2 hours, at -50° C., with solutions of 12.7 g (0.11 mol) of sulfamoyl chloride and 11.1 g (0.11 mol) of triethylamine each in 100 ml of tetrahydrofuran, the mixture was brought from -50° to 20° C. over a period of 2 hours and filtered, the filtrate was evaporated to dryness in vacuo and the residue was chromatographed on 400 g of silica gel with methylene chloride. After recrystallization from isopropanol, the main fraction yielded 9.7 g (54.8% of theory, based on enamine) of 2-oxocyclohexanesulfonamide of melting point 118°-119° C.

Provenance & Evidence