V. G. Pesin, E. K. D'yachenko
1967
Citations
0
Influential Citations
2
Citations
Journal
Chemistry of Heterocyclic Compounds
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.