Russian Journal of Applied Chemistry

, Volume 84, Issue 3, pp 400–406 | Cite as

Thermodynamic and kinetic aspects of a single-reactor synthesis of 5-amino-3-methyl-1,2,4-triazole hydrochloride from aminoguanidine and acetic acid

  • E. V. Tarasova
  • V. M. Chernyshev
  • A. V. Chernysheva
  • R. S. Abagyan
Organic Synthesis and Industrial Organic Chemistry


Fundamental thermodynamic and kinetic aspects of the reaction in which acetic acid guanyl hydrazide is formed from aminoguanidine and acetic acid in aqueous solutions at pH 0.6-1.5 and the kinetics of cyclization of acetic acid guanyl hydrazide hydrochloride to 5-amino-3-methyl-1,2,4-triazole hydrochloride in a melt were studied. Methods for synthesis of acetic acid guanyl hydrazide hydrochlorides and 5-amino-3-methyl-1,2,4-triazole hydrochloride were developed.


Triazole Hydrazide AcOH Malonic Acid Aminoguanidine 
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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Temple, C., Chemistry of Heterocyclic Compounds, vol. 37, Montgomery, J.A., Ed., New York: Wiley, 1981, pp. 103–204.CrossRefGoogle Scholar
  2. 2.
    Curtis, A.D.M., Sci. Synth., 2004, vol. 13, pp. 603–639.Google Scholar
  3. 3.
    Dolzhenko, A.V., Pastorin, G., Dolzhenko, A.V., and Chui, W.-K., Tetrahedron Lett., 2009, vol. 50, no. 18, pp. 2124–2128.CrossRefGoogle Scholar
  4. 4.
    Grinshtein, V.Ya. and Chipen, G.I., Zh. Obshch. Khim., 1961, vol. 31, no. 3, pp. 886–890.Google Scholar
  5. 5.
    Huang, Y., Hu, X.-Q., Shen, D.-P., and Fei, Y., Mol. Divers., 2007, vol. 11, no. 2, pp. 73–80.CrossRefGoogle Scholar
  6. 6.
    Abdel-Megeed, A.M., Abdel-Rahmana, H.M., Alkaramanya, G.-E.S., and El-Gendya, M.A., Eur. J. Med. Chem., 2009, vol. 44, no. 1, pp. 117–123.CrossRefGoogle Scholar
  7. 7.
    Chernysheva, A.V., Chernyshev, V.M., Korolenko, P.V., and Taranushich, V.A., Zh. Prikl. Khim., 2008, vol. 81, no. 10, pp. 1690–1695.Google Scholar
  8. 8.
    Chernyshev, V.M., Chernysheva, A.V., and Taranushich, V.A., Zh. Prikl. Khim., 2009, vol. 82, no. 2, pp. 282–287.Google Scholar
  9. 9.
    Chipen, G.I. and Grinshtein, V.Ya., Izv. Akad. Nauk LatvSSR, 1965, no. 2, pp. 204–208.Google Scholar
  10. 10.
    Chupakhin, O.N., Ulomsky, E.N., Deev, S.L., and Rusinov, V.L., Synth. Commun., 2001, vol. 31, no. 15, pp. 2351–2355.CrossRefGoogle Scholar
  11. 11.
    Reilly, J. and Drumm, P.J., J. Chem. Soc., 1926, vol. 50, pp. 1729–1737.CrossRefGoogle Scholar
  12. 12.
    Atkinson, M.R., Kozmak, A.A., Parkes, E.A., and Polya, J.B., J. Chem Soc., 1954, vol. 78, no. 12, pp. 4508–4510.CrossRefGoogle Scholar
  13. 13.
    Barnett, E.D.B., Goodway, N.F., Kermack, W.O., et al., J. Chem. Soc., 1929, vol. 53, pp. 813–816.CrossRefGoogle Scholar
  14. 14.
    Lipinski, C.A., J. Med. Chem., 1983, vol. 26, no. 1, pp. 1–6.CrossRefGoogle Scholar
  15. 15.
    Lopyrev, V.A. and Rakhmatullina, T.N., Zh. Obshch. Khim., 1982, vol. 53, no. 7, p. 1684.Google Scholar
  16. 16.
    Koskinen, M., Mutikainen, I., Tilus, P., et al., Monatsh. Chem., 1997, vol. 128, nos. 8–9, pp. 767–775.CrossRefGoogle Scholar
  17. 17.
    Al’bert, A. and Serzhent, E., Konstanty ionizatsii kislot i osnovamii (Constants of Acids and Bases Ionizations), Miscow: Khimiya, 1964.Google Scholar
  18. 18.
    Brown, R.S., Bennet, A.J., and Slebocka-Tilk, H., Acc. Chem. Res., 1992, vol. 25, no. 11, pp. 481–488.CrossRefGoogle Scholar
  19. 19.
    Pan, B., Ricci, M.S., and Trout, B.L., J. Phys. Chem. B, 2010, vol. 114, no. 13, pp. 4389–4399.CrossRefGoogle Scholar
  20. 20.
    Lebedev, N.N., Manakov, M.N., and Shvets, V.F., Teoriya tekhnologicheskikh protsessov osnovnogo organicheskogo i neftekhimicheskogo sinteza (Theory of Technological Processes of Basic Organic and Petrochemical Synthesis), Moscow: Khimiya, 1975.Google Scholar
  21. 21.
    Chernyshev, V.M., Chernysheva, A.V., Tarasova, E.V., et al., Acta Cryst. Sect. E, 2010, vol. 66, pp. 1152–1153.CrossRefGoogle Scholar
  22. 22.
    Anders, E., Wermann, K., Wiedel, B., and Vanden Eynde, J.-J., Liebigs. Ann., 1997, no. 4, pp. 745–752.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  • E. V. Tarasova
    • 1
  • V. M. Chernyshev
    • 1
  • A. V. Chernysheva
    • 1
  • R. S. Abagyan
    • 1
  1. 1.South-Russian State Technical University (Novocherkassk Polytechnic Institute)Novocherkassk, Rostov-on-Don oblastRussia

Personalised recommendations