Acetic Anhydride → N-(4-Chlorobut-2-yn-1-yl)acetamide

Participants

Reaction Steps

1-Amino-4-chloro-2-butyne hydrochloride (59.75 g) was dissolved in 10% aqueous sodium acetate-solution (335 ml). Ethyl acetate (500 ml) was added, and acetic anhydride (70 ml) was added dropwise at room temperature. A 25% aqueous sodium acetate solution was added to pH 5 and the solution was stirred for 30 min at room temperature. The ethyl acetate layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with water, brine and dried over sodium sulphate, filtered and evaporated in vacuo yielding 1-acetylamino4-chloro-2-butyne as a yellow syrup (58.8 g).

Provenance & Evidence