Chemistry of Heterocyclic Compounds

, Volume 2, Issue 4, pp 399–401 | Cite as

Researches on 2, 1, 3-thia- and selenadiazole

XLI. Chloromethylation of benzo-2, 1, 3-selenadiazole and its 4- and 5-methyl derivatives
  • V. G. Pesin
  • E. K. D′yachenko


Depending on the reaction conditions, benzo-2, 1, 3-selenadiazole (I), dichlorodimethyl ether and aluminum chloride react to give a complex IV, or else 4-chloromethyl-(V) or 4, 7-di(chloromethyl) benzo-2, 1, 3-selenadiazole (VI). 5-(II) and 4-methylbenzo-2,l,3-selenadiazole(III) are chloromethylated by dichlorodimethyl ether in the presence of chlorosulfonic acid. Compound II is converted mainly into 5-methyl-4-chloromethylbenzo-2, 1, 3-selenadiazole(VII) or a mixture of three possible isomers VII, VIII, and IX, depending on the amount of base or pseudo-base in the reaction mixture. Ill gives mainly 4-methyl-7-chlorornethylbenzo-2, 1, 3-selenadiazole(X), independent of the presence of base. The structures of the chloromethylation products are shown by reductive splitting to o-diamides, and chromatography of the latter in the presence of reference spots. The high reactivity of the chlorine in the chloromethyl group made it possible to obtain new derivatives by replacing it with a hydroxyl, cyano, or thiocyano group.


Aluminum Ether Chloride Chromatography Hydroxyl 
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Copyright information

© The Faraday Press, Inc. 1967

Authors and Affiliations

  • V. G. Pesin
    • 1
  • E. K. D′yachenko
    • 1
  1. 1.Leningrad Pharmaceutical Chemistry InstituteUSSR

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