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Reactions of 2-aminobenzothiazoles with ethylene chlorohydrin. molecular and crystal structure of bis[(3-β-hydroxyethyl)benzo-thiazolyl-2-indene]ammonium chloride

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Hydroxyethylation of 2-aminobenzothiazoles by ethylene chlorohydrin unexpectedly led to preferential formation of 3-β-chloroethylbenzothiazolin-2-one. In the case of unsubstituted 2-aminobenzothiazole, we also isolated the target 2-indno-3-β-hydroxyethylbenzothiazoline and bis((3-/3-hydroxyethyl)benzothiazolyl-2-indenelamnionium chloride. As a result of reaction of 2-aminobenzothiazole with 3-β-chloroethylbenzothiazolin-2-one, we obtained 2-(benzothiazolyl-2-imino)-3-(β-(2-oxobenzothiazolin-3-yl)ethyllbenzothiazoline. The structure ofthesynthesized compounds was established based on x-ray diffraction, PMR, IR, UV, and mass spectra.

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References

  1. P. M. Kochergin, I. A. Mazur, and B. E. Mandrichenko, USSR Inventor's Certificate 427012; Byull. Izobret., No. 17, 102 (1974).

  2. A. Kreutzberger and B. Meyer, Arch. Pharm.,309, 643 (1976).

    Google Scholar 

  3. A. F. Vlasenko, B. E. Mandrichenko, G. K. Rogul'chenko, R. S. Sinyak, I. A. Mazur, and P. M. Kochergin, Khim. Geterotsikl. Soedin., No. 6, 834 (1976).

  4. D. B. Kuhla, US Pat. 4097598; Ref. Zh. Khim., 90217P (l979).

  5. A. M. Simonov and P. M. Kochergin, Khim. Geterotsiki. Soedin., No. 2, 317 (1965).

  6. V. A. Anisimova, M. V. Levchenko, and A. F. Pozharskii, Khim. Geterotsikl. Soedin., No. 7, 918 (1986).

  7. V. A. Anisimova, M. V. Levchenko, T. B. Korochina, A. A. Spasov, S. G. Kovalev, and G. P. Dudchenko, Eur. Pat. 571,253; Chem. Abstr.,120, 245099 (l994).

    Google Scholar 

  8. R. von Altmann, Acta Crystallogr.,22, 246 (1967).

    Google Scholar 

  9. J. L. Flippen, Phosphorus and Sulfur,3, 185 (1977).

    Google Scholar 

  10. R. Benassi, R. Grandi, U. M. Pagnoni, F. Taddei, G. Bocelli, and P. Sgarabotto, Chem. Soc. Perkin II, No. 10, 1513 (1985).

  11. E. Bayer and G. Hafelinger, Chem. Ber.,99, 1689 (1966).

    Google Scholar 

  12. G. M. Sheldrick, Acta Crystallogr.,A46, 467 (1990).

    Google Scholar 

  13. G. M. Sheldrick, SHELXS-76: Program for Crystal Structure Determination, Cambridge, England.

  14. P. Sohar, G. H. Denny, and R. D. Babson, J. Heterocycl. Chem.,6, 163 (1969).

    Google Scholar 

  15. M. R. Yagudaev, L. P. Kosmacheva, and R. F. Ambartsumova, Khim. Geterotsiki. Soedin., No. 7, 1265 (l991).

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Authors
  1. M. K. Makhmudov
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  2. R. F. Ambartsumova
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  3. B. Tashkhodzhaev
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Additional information

Institute of the Chemistry of Plant Compounds, Academy of Sciences of the Uzbekistan Republic, Tashkent 700170. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1273–1278, September, 1996. Original article submitted March 19, 1996.

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Makhmudov, M.K., Ambartsumova, R.F. & Tashkhodzhaev, B. Reactions of 2-aminobenzothiazoles with ethylene chlorohydrin. molecular and crystal structure of bis[(3-β-hydroxyethyl)benzo-thiazolyl-2-indene]ammonium chloride. Chem Heterocycl Compd 32, 1095–1099 (1996). https://doi.org/10.1007/BF01164719

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