Triethylamine → 2-chloro-(2',2'-dimethylpropionamido)-N,N-dimethylbenzamide

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Reaction Steps

4-Amino-2-chloro-N,N-dimethylbenzamide (1.0 g) and triethylamine (1.21 g) were dissolved in methylene chloride (20 ml) and the solution was cooled to 0°-5° C. 2,2-Dimethylpropionyl chloride (1.21 g) was added dropwise keeping the temperature below 10° C. and the resulting orange solution stirred at 0°-10° C. for 0.5 hour. The organic solution was then washed with aqueous sodium bicarbonate and then water, dried and evaporated to give an orange solid. This was recrystallised from 3:1 ethyl acetate:chloroform to give 2-chloro-(2',2'-dimethylpropionamido)-N,N-dimethylbenzamide as an off-white crystalline solid (1.027 g), m.p. 202°-203° C.

Provenance & Evidence