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On interaction of 2-aminobenzothiazoles with halohydrins

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Interaction of 2-aminobenzothiazoles with ethylene chlorohydrin on boiling leads mainly to formation of the corresponding 3-(β-chloroethyl)benzothiazolin-2-ones. Reducing the reaction temperature increases the fraction of 2-imino-(3-β-hydroxyethyl)benzothiazolines. In both instances formation of bis[3-(β-hydroxyethyl)benzothiazol-2-ylidene]ammonium chlorides is observed. The reaction of 2-aminobenzothiazole with propylene bromohydrin gives only the corresponding amino alcohols. The anomalous products from the reaction of β-chloroethyl derivatives of benzothiazolinones result from a dominating side reaction of the starting 2-aminobenzothiazoles with the ethylene chlorohydrin thermolysis products that are formed on boiling.

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Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent 700170. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 981–987, July, 1999.

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Ambartsumova, R.F. On interaction of 2-aminobenzothiazoles with halohydrins. Chem Heterocycl Compd 35, 860–865 (1999). https://doi.org/10.1007/BF02252113

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  • Alcohol
  • Chloride
  • Ammonium
  • Propylene
  • Reaction Temperature