Water → 2-chloro-2',6'-dimethyl-N-(4,5-dichloroimidazol-1-yl-methyl)-acetanilide

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Reaction Steps

A solution of 13.7 parts by weight of 4,5-dichloroimidazole and 4.4 parts by weight of sodium hydroxide in 20 parts of water was added dropwise to a solution of 24.6 parts by weight of 2-chloro-N-chloromethyl-2',6'-dimethylacetanilide and 2.0 parts by weight of triethylbenzylammonium chloride in 50 parts by volume of dichloromethane at 20°-25° C., with vigorous stirring, which was continued for 2 hours. The organic phase was washed with three times 30 parts by volume of water, dried over sodium sulfate and evaporated under reduced pressure at 70° C., to give 29.9 parts by weight of 2-chloro-2',6'-dimethyl-N-(4,5-dichloroimidazol-1-yl-methyl)-acetanilide of melting point 99° C.; the product was pure according to the 1H-NMR spectrum and according to thin layer chromatography carried out with a 3:7 ethyl acetate:toluene mixture.

Provenance & Evidence