The Reactions of Hydrazine Derivatives with Carbon Disulfide

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  • KOBAYASHI Yukio
    Department of Chemistry, Faculty of Science, Tokai University
  • MINUNG Lee
    Department of Chemistry, Faculty of Science, Tokai University
  • SHIRAI KOZO
    Department of Chemistry, Faculty of Science, Tokai University

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Other Title
  • 脂肪族ヒドラジン誘導体と二硫化炭素との反応

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Description

The reactions of the free bases of aliphatic hydrazine derivatives with carbon disulfide were investigated in an aqueous sodium hydroxide solution. Aminoguanidine gave 2, 5-dimercapto1, 3, 4-thiadiazole (DMTD, 94%) and thiourea (50%). The result could be explained by the nucleophilic addition of the hydrazino group of aminoguanidine to carbon disulfide followed by the cleavage of the adduct into DMTD and cyanamide under the strong basic conditions. The latter was further converted to thiourea by the reaction with hydrogen sulfide. The reaction of other hydrazine derivatives such as thiosernicarbazide or semicarbazide gave DMTD under similar reaction conditions. The reaction of semicarbazide hydrochloride with carbon disulfide in pyridine at 45∼50°C for 4 h gave 1, 5-dicarbamoylthiocarbohydrazide (DCTH, 89%) via thermally unstable pyridinium semicarbazide-1-carbodithioate (PSDTC). When the reaction was stopped after 1 h, only intermediate PSDTC was isolated in 92% yield.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1981 (8), 1295-1298, 1981-08-10

    The Chemical Society of Japan

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