Hydrochloric Acid → N-(1-Cyano-1-methylethyl)-2-(methylthio)ethanesulfonamide

Participants

Reaction Steps

To a solution of 8.2 g (0.0470 moles) N-(2-cyano-2-propyl)-vinylsulfonamide (the product of Example 26) in 30 ml methanol, 32 ml of a 1.5M solution of methanethiol was added over 5 minutes. A small amount (a few mg) of potassium carbonate was added to the mixture and it was stirred overnight at room temperature. The reaction mixture was warmed to about 30° C., more methanethiol/methanol solution (about 10 ml) was added, and the resulting mixture was stirred at 30° C. for four hours. The mixture was acidified with 10% hydrochloric acid and then evaporated to afford 10.0 g of a pale yellow oil. The oil was dissolved in methylene chloride, filtered and evaporated to dryness. The residue was purified by flash chromatography with 30% hexane in ethyl acetate to give 9.3 g of the above-identified product, as a colorless oil which crystallized upon standing.

Provenance & Evidence