Triethylamine → S-methyl N-[N'-methyl-N'-(dimethylaminosulfenyl)-carbamoyloxy]thioacetimidate

Participants

Reaction Steps

A mixture of 5.25 g (0.05 mole) of S-methyl-N-hydroxythioacetimidate, 7.9 g of N-methyl-N-(dimethylaminosulfenyl)carbamoyl fluoride, and 5.1 g of triethylamine in 75 ml of tetrahydrofuran was stirred and heated at 40°-60° C. for 3 hrs. and then at 25° C. for 8 hrs. The solvent was removed in vacuo, and the residue was taken up in chloroform. This solution was extracted with water and 10% potassium carbonate, dried (MgSO4) and then was concentrated in vacuo. The crude syrupy residue obtained was purified by column chromatography on silica gel to give 1.6 g of S-methyl N-[N'-methyl-N'-(dimethylaminosulfenyl)-carbamoyloxy]thioacetimidate, a yellow syrup.

Provenance & Evidence