Chemistry of Heterocyclic Compounds

, Volume 35, Issue 7, pp 860–865 | Cite as

On interaction of 2-aminobenzothiazoles with halohydrins

  • R. F. Ambartsumova


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.


Alcohol Chloride Ammonium Propylene Reaction Temperature 
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© Kluwer Academic/Plenum Publishers 1999

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  • R. F. Ambartsumova

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