The synthesis of N-[4-methyl(41-chlorophenyl)-2-R-phenylіmіnothіazol-3-yl]-morpholine derivatives by Hantzsch reaction

Authors

  • L. O. Perekhoda National University of Pharmacy, Ukraine
  • H. O. Yeromina National University of Pharmacy, Ukraine
  • I. V. Drapak Lviv National Medical University named after Danylo Halytsky, Ukraine
  • I. A. Sych National University of Pharmacy, Ukraine
  • A. M. Demchenko Institute of Pharmacology and Toxicology of the AMS of Ukraine, Ukraine
  • S. O. Komykhov State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.16.890

Keywords:

2-R-phenyliminothiazole derivatives, synthesis, Hantzsch reaction, physical and chemical properties

Abstract

Continuing the search for biologically active substances among 2-R-phenylіmіnothіazole derivatives a new series of N-[4-methyl(41-chlorophenyl)-2-R-phenylіmіnothіazol-3-yl]-morpholine derivatives has been synthesized by Hantzsch reaction. Hydrochlorides of N-[4-methyl-2-R-phenylіmіnothіazol-3-yl]-morpholine 3 and hydrobromides of N-[4-(41-chlorophenyl)-2-R-phenylіmіnothіazol-3-yl]-morpholine 5 were obtained by boiling the equimolar amounts of asymmetric thioureas 1 with α-chloroacetone 2 and α-bromo-4-chloroacetophenone 4, respectively, in the ethanol medium. N-[4-(41-Chlorophenyl)-2-R-phenylіmіnothіazol-3-yl]-morpholine 6 were obtained by neutralizing compounds 5 using 10% NH4OH solution. Satisfactory yields of compounds 3, 5, 6 were obtained within 1-3 hours. N-[4-methyl(41-chlorophenyl)-2-R-phenylіmіnothіazol-3-yl]-morpholine derivatives 3, 5, 6 were crystallized from organic solvents and obtained with the yields of 74-87%. The structures and purity of 3, 5, 6 have been confirmed by elemental analysis, 1H NMR-spectra and chromato-mass spectroscopy. As a result of Hantzsch reaction formation of two isomeric structures is possible. Therefore, to determine a true structure of the compounds obtained NMR spectroscopy with its special techniques was used. The studies have been conducted on the example of the reaction product 6i, and it has been proven that this structure is exactly N-[4-(41chlorophenyl)-2-(4’-chlorophenylimino)thiazol-3-yl]-morpholine 6i. Based on the research results of the structure of the compounds synthesized a possible mechanism of the reaction studied has been proposed.

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References

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Published

2016-09-19

How to Cite

(1)
Perekhoda, L. O.; Yeromina, H. O.; Drapak, I. V.; Sych, I. A.; Demchenko, A. M.; Komykhov, S. O. The Synthesis of N-[4-methyl(41-Chlorophenyl)-2-R-phenylіmіnothіazol-3-Yl]-Morpholine Derivatives by Hantzsch Reaction. J. Org. Pharm. Chem. 2016, 14, 52-57.

Issue

Vol. 14 No. 3(55) (2016)

Section

Original Researches

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Copyright (c) 2016 National University of Pharmacy

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