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Chemistry of Heterocyclic Compounds

, Volume 3, Issue 6, pp 818–820 | Cite as

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

XLIX. The chloromethylation of benzo-2,1, 3-thiadiazole
  • V. G. Pesin
  • E. K. D'yachenko
Article

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.

Keywords

Carboxy Dimethylformamide Aluminum Chloride Formyl Chloromethyl 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    I. Schreiber, Chem. Listy, 282, 1961.Google Scholar
  2. 2.
    V. G. Pesin, A. M. Khaletskii, and V. A. Sergeev, ZhOKh, 33, 949, 1963.Google Scholar
  3. 3.
    Organic Syntheses [Russian translation], IL, Moscow, 8, 73, 1958.Google Scholar
  4. 4.
    E. Bala, Z. Dumitrescu, and I. Marcus, Pharmazie, 16, 357, 1961; RZhKh, 11Zh 452, 1962.Google Scholar
  5. 5.
    Ya. L. Gol'dfarb and Yu. B. Vol'kenshtein, ZhOKh, 31, 616, 1961.Google Scholar
  6. 6.
    A. A. Akhrem and A. I. Kuznetsova, Usp. khim., 32, 823, 1935; Thin-Layer Chromatography [in Russian], Nauka, Moscow, 1964.Google Scholar
  7. 7.
    S. J. Angyal, Organic Reactions [Russian translation], IL, Moscow, 8, 268, 1956.Google Scholar
  8. 8.
    F. Kronke and H. Schmeiss, Ber., 72, 440, 1939.Google Scholar
  9. 9.
    V. G. Pesin, A. M. Khaletskii, and Chao Chihchung, ZhOKh, 27, 1570, 1957.Google Scholar
  10. 10.
    V. G. Pesin, I. G. Vitenberg, and A. M. Khaletskii, ZhOKh, 34, 1272, 1964.Google Scholar
  11. 11.
    V. G. Pesin and V. A. Sergeev, KhGS [Chemistry of Heterocyclic Compounds], 950, 1967.Google Scholar

Copyright information

© The Faraday Press, Inc. 1970

Authors and Affiliations

  • V. G. Pesin
    • 1
  • E. K. D'yachenko
    • 1
  1. 1.Leningrad Chemical and Pharmaceutical InstituteUSSR

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