Hydrochloric Acid → 6-(Hydroxyimino)-5,5-dimethylthiomorpholin-3-one

Participants

Reaction Conditions

Reaction Steps

A solution of 41 g α-aminoisobutyraldoxime hydrochloride and 150 ml. of water was charged into a stirred flask and cooled to 0° C. Chlorine was added to the solution at 0° C until 22 g. had been taken up. The reaction mixture was stirred at 0° C for 30 minutes after the chlorine addition. Sodium hydroxide (6 g in 40 ml water) was added with stirring to neutralize the hydrochloric acid, after which a solution of 36 g of ethyl mercaptoacetate and 12 g of sodium hydroxide in 40 ml of water was added rapidly at 5° to 10° C. The mixture was warmed to 25° C and stirred overnight. The solid product was filtered, washed with water then dried at room temperature, to yield 7 g of 2-oximino-3,3-dimethyltetrahydro-1,4-thiazin-5-one, m.p. 234°-236° C. An nmr spectrum and m.p. comparison showed the product to be identical with that from Example II.

Provenance & Evidence