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

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Reaction Steps

A solution of 10.8 parts by weight of 4-methoxypyrazole and 4.0 parts by weight of sodium hydroxide in 20 parts by volume of water was added dropwise at 10°-15° C., with vigorous stirring, to a solution of 24.6 parts by weight of 2-chloro-N-chloromethyl-2',6'-dimethylacetanilide and one part by weight of benzyltriethylammonium bromide in 70 parts by volume of toluene and the stirring was continued for 3 hours. The organic phase was washed with three times 40 parts by volume of water, dried over sodium sulfate and evaporated in vacuo at 80° C. to give 28.1 parts by weight of 2-chloro-2',6'-dimethyl-N-(4-methoxypyrazol-1-yl-methyl)acetanilide of melting point 115°-116° C. (melting point of a sample recrystallized from ethanol: 118° C.), which according to the 1H-NMR spectrum and thin layer chromatography carried out using a 3:7 mixture of ethyl acetate:toluene was more than 97% pure.

Provenance & Evidence