Hydrochloric Acid → 5-(4-Methoxy-benzyl)-[1,3,4]oxathiazol-2-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-methoxyphenylacetamide (5.06 g, 30.0 mmol) in toluene (10 mL) was added 2,6-di-t-butyl-4-hydroxytoluene (132 mg, 0.60 mmol) and chlorocarbonylsulfenyl chloride (5.52 mL, 60.0 mmol). The resulting mixture was warmed to 115° C. for 80 min during which time hydrochloric acid gas was evolved resulting in a yellow solution. To this solution additional chlorcarbonyl-sulfenylchloride (1.38 mL, 15.00 mmoles) was added and the mixture heated for 40 min and allowed to stand at room temperature overnight. The reaction mixture was cooled to 0° C. and stirred for 10 min before being filtered to remove a beige solid. The solid was washed with cold toluene (2×10 mL) and the filtrate was concentrated and purified by flash chromatography (silica gel, 20% ethyl acetate/hexanes) which afforded 5-(4-methoxy-benzyl)-[1,3,4]oxathiazol-2-one (1.12 g, 17%) as a yellow solid.

Provenance & Evidence