Acetic Anhydride → N-(1,1-dimethylethyl)-N-(3,3,3-trichloro-2-hydroxypropyl)acetamide

Participants

Reaction Steps

To a stirred suspension of 5 grams of 3-(1,1-dimethylethylamino)-1,1,1-trichloro-2-propanol in 75 grams of dichloromethane at -60° C., 2.2 grams of acetic anhydride was added dropwise during 15 minutes. After the reaction mixture was allowed to warm to ambient temperature during 1 hour, the mixture was stirred for 2 hours. The solution was washed with 100 grams of saturated aqueous sodium bicarbonate, dried with anhydrous sodium sulfate and evaporated under a reduced pressure of 100 mm. Hg to 3.9 grams of an oil. The oil was crystallized from methylcyclohexane to yield 1.4 gram of white N-(1,1-dimethylethyl)-N-(3,3,3-trichloro-2-hydroxypropyl)acetamide melting 124°-126° C.

Provenance & Evidence