Sodium hydride → N-(4-chloro-alpha,alpha-dimethylbenzyl)-2-(2-dimethylcarbamoyl-phenoxy)acetamide

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Reaction Steps

A mixture of the 2-hydroxy-N,N-dimethylbenzamide (0.68 g) in DMSO (5 ml) was added to a stirred suspension of sodium hydride (163 mg of a 60% dispersion in mineral oil) in DMSO (5 ml) at ambient temperature over 5 minutes with stirring. The mixture was stirred until the evolution of hydrogen ceased and then a solution of 2-chloro-N-[1-(4-chlorophenyl)-1-methylethyl]-acetamide (prepared by reacting α,α-dimethylbenzylamine with chloroacetyl chloride) (1.0 g) in DMSO (5 ml) was added dropwise over 5 minutes with stirring. The mixture was stirred at ambient temperature for 16 hours and then poured into ice water (200 ml) and extracted with ethyl acetate to give a solid which was recrystallised from ethyl acetate/petroleum ether, b.p. 60°-80° C. to give N-(4-chloro-α,α-dimethylbenzyl)-2-(2-dimethylcarbamoyl-phenoxy)acetamide, m.p. 127°-9° C.

Provenance & Evidence