Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

On interaction of 2-aminobenzothiazoles with halohydrins

  • 39 Accesses

  • 4 Citations

Abstract

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.

This is a preview of subscription content, log in to check access.

References

  1. 1.

    R. F. Ambartsumova,Zh. Org. Khim.,29, 2320 (1993).

  2. 2.

    M. K. Makhmudov, R. F. Ambartsumova, and B. Tashkhodzhaev,Khim. Geterotsikl. Soedin., No. 9, 1273 (1996).

  3. 3.

    I. F. Tupitsyn, N. N. Zatsepina, and A. I. Belyashova,Khim. Geterotsikl. Soedin., No. 9, 1235 (1984).

  4. 4.

    O. Attanasi, G. Bartoli, and P. E. Todesco,J. Heterocycl. Chem.,13, 1021 (1976).

  5. 5.

    I. E. Zil'berman, V. A. Kolesnikov, S. M. Danov, R. V. Efremov, and E. V. Pantina,Zh. Prikl. Khim.,58, 2529 (1985).

  6. 6.

    I. E. Zil'berman, V. A. Kolesnikov, S. M. Danov, and R. V. Efremov,Zh. Org. Khim.,25, 603 (1989).

  7. 7.

    T. Papenfuhs, German Patent 2947489;Chem. Abstr.,95, 97784 (1981).

  8. 8.

    V. A. Kolesnikov, I. E. Zil'berman, S. M. Danov, and R. V. Efremov,Zh. Prikl. Khim.,59, 2579 (1986).

  9. 9.

    R. F. Ambartsumova and S. R. Tulyaganov,Zh. Org. Khim.,7, 1962 (1971).

  10. 10.

    P. B. Terent'ev and A. P. Stankyavichyus,Mass-Spectrometric Analysis of Biologically Active Nitrogen Bases [in Russian], Mokslas, Vilnius (1987), p. 129.

  11. 11.

    C. G. Stuckwisch,J. Am. Chem. Soc.,71, 3417 (1949).

  12. 12.

    R. Q. Brewster and F. B. Dains,J. Am. Chem. Soc.,58, 1364 (1936).

  13. 13.

    F. H. Jackson and A. T. Peters,J. Chem. Soc. C, No. 2, 268 (1969).

  14. 14.

    G. Sieber and J. Ulbricht,J. Prakt. Chem.,20, 14 (1963).

Download references

Additional information

Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent 700170. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 981–987, July, 1999.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Ambartsumova, R.F. On interaction of 2-aminobenzothiazoles with halohydrins. Chem Heterocycl Compd 35, 860–865 (1999). https://doi.org/10.1007/BF02252113

Download citation

Keywords

  • Alcohol
  • Chloride
  • Ammonium
  • Propylene
  • Reaction Temperature