Triethylamine → Acesulfame

Participants

Reaction Steps

A mixture, with a total volume of 50 ml, of 40.4 g (0.4 mol) of triethylamine and liquid SO2 was added dropwise, at -10° C., to a solution of 20.2 g (0.2 mol) of acetoacetamide and 23.7 g (0.2 mol) of chlorosulfonyl fluoride in 70 ml of liquid SO2. The mixture was stirred for 2 hours and the liquid SO2 was then distilled off, a vacuum being applied at the end. The residue was added dropwise to 400 ml of aqueous NaOH, acidified with concentrated hydrochloric acid, with ice-cooling, and extracted with ethyl acetate. After treatment of the ethyl acetate phase with animal charcoal and Na2SO4, the extract was evaporated in vacuo. 15 g (approx. 20% of theory) of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide were obtained.

Provenance & Evidence