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Studies in the field of 2, 1, 3-Thiadiazole and 2,1, 3-Selenadiazole

XLIX. The chloromethylation of benzo-2,1, 3-thiadiazole

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Benzo-2, 1, 3-thiadiazole (I) undergoes chloromethylation with dichlorodimethyl ether in the presence of anhydrous aluminum chloride with the predominant formation of 4, 7-di(chloromethyl)benzo-2, 1, 3-thiadiazole (II). Bases and pseudobases (paraformaldehyde, hexamethylenetetramine, dimethylformamide) exert an inhibiting influence on this reaction. In the presence of these substances, a mixture of compound II and 4-(chloromethyl)benzo-2, 1, 3-thiadiazole (III) is formed, or else no reaction takes place. The structures of compounds II and III has been shown by their reductive decomposition to o-diamines described in the literature. The high reactivity of the chlorine in the chloromethyl group has enabled various new derivatives of benzo-2, 1, 3-thiadiazole to be obtained by its replacement with hydroxy, thiocyanato, di(β-hydroxyethyl)amino, di(β-chloroethyl)amino, formyl, and carboxy groups.

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Authors and Affiliations

  1. Leningrad Chemical and Pharmaceutical Institute, USSR

    V. G. Pesin & E. K. D'yachenko

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  1. V. G. Pesin
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  2. E. K. D'yachenko
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Additional information

For communication XLVIII, see [11].

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Pesin, V.G., D'yachenko, E.K. Studies in the field of 2, 1, 3-Thiadiazole and 2,1, 3-Selenadiazole. Chem Heterocycl Compd 3, 818–820 (1967). https://doi.org/10.1007/BF00474878

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