Conditions for the Selective Conversion of Quaternary 3-Anilino-1,5-dimethylpyrazolium Salts into 3-Anilino-1,5-dimethylpyrazole |
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Authors: | I B Dzvinchuk S A Kartashov A V Vypirailenko U Doller M O Lozinskii |
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Institution: | (1) Institute of Organic Chemistry, National Academy of Sciences of the Ukraine, Kiev, 02094;(2) Aventis CropScience Gmbh, D-65926 Frankfurt-on-Main, Germany |
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Abstract: | The possibility has been studied of converting quaternary 3-anilino-1,5-dimethylpyrazolium salts into 3-anilino-1,5-dimethylpyrazole, the first representative of the 1-alkyl-3-arylaminopyrazoles. The dependence of the reaction direction on the nature of the substituent at position 2 has been clarified. The most effective result was obtained with a cyanoethyl substituent. On boiling the initial salt with aqueous ammonia the target product is isolated in quantitative yield. Syntheses of the initial salts are described. C-Sulfonation was detected on interacting 3-anilino-1-benzoyl-3-methylpyrazole and dimethyl sulfate, with the formation of p-(3-amino-1,2,5-trimethylpyrazolio)benzenesulfonate. |
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Keywords: | hydrazines pyrazoles dehaloalkylation quaternization selectivity C-sulfonation cyanoethylation |
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