Hydrochloric Acid → N-acetyl-N-ethyl-2-(acetylthio)acetamide

Participants

Reaction Steps

A solution of 11 g. (0.063 mole) of N-acetyl-2-(acetylthio)acetamide in 75 ml. of dry dimethylformamide was cooled to -30° C. and there was then added 3.02 g. (0.063 mole) of 50% sodium hydride. The reaction mixture was aged until hydrogen evolution ceased. There was then added 5.1 ml. (0.063 mole) of ethyl iodide after cooling the reaction mixture to -40° C., after which the reaction mixture was allowed to come to room temperature and age overnight. A precipitate formed. There was next added 5 ml. of acetic acid, then 100 ml. of ether, followed by 30 ml. of 2.5 N hydrochloric acid and 70 ml. of water. The ether layer was separated and the water layer was increased to about 400 ml. with water, after which it was extracted three times with 100 ml. of ether. The ether extract was dried over magnesium sulfate and concentrated to an oil of 7.2 g. Composition of the product was verified by NMR and mass spectrometry.

Provenance & Evidence