Abstract
The influence of the molar ratio and concentration of the reactants and of the temperature and time of the synthesis on the yield of malonic acid guanylhydrazides in the reaction of aminoguanidine with malonic acid in acidic aqueous solutions was examined, and improved procedures for preparing 5-amino-1,2,4-triazol-3-ylacetic acid and bis(5-amino-1,2,4-triazol-3-yl)methane were suggested.
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Dervan, P.B., Bioorg. Med. Chem., 2001, vol. 9, no. 9, pp. 2215–2235.
Dzygiel, A., Rzeszotarska, B., Masiukiewicz, E., et al., Chem. Pharm. Bull., 2004, vol. 52, no. 2, pp. 192–198.
Masiukiewicz, E., Rzeszotarska, B., Wawrzycka-Gorczyca, I., and Koodziejczyk, E., Synth. Commun., 2007, vol. 37, no. 11, pp. 1917–1925.
US Patent 5990084.
US Patent 5064953.
Kofman, T.P., Uvarova, T.A., Kartseva, G.Yu., and Uspenskaya, T.L., Zh. Org. Khim., 1997, vol. 33, no. 12, pp. 1867–1876.
Chernyshev, V.M., Chernysheva, A.V., and Taranushich, V.A., Zh. Prikl. Khim., 2006, vol. 79, no. 5, pp. 792–795.
Pevzner, M.S., Ross. Khim. Zh., 1997, vol. 41, no. 2, pp. 73–83.
Kisileva, V.V., Gakh, A.A., and Fainzil’berg, A.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1990, no. 9, pp. 2075–2094.
USSR Inventor’s Certificate no. 3204967.
Kofman, T.P., Uvarova, T.A., and Kartseva, G.Yu., Zh. Org. Khim., 1995, vol. 31, no. 2, pp. 271–275.
Chernysheva, A.V., Chernyshev, V.M., Korolenko, P.V., and Taranushich, V.A., Zh. Prikl. Khim., 2008, vol. 81, no. 10, pp. 1690–1695.
US Patent 2744116.
Barmin, M.I., Kartavykh, V.P., Korolev, E.A., et al., Zh. Obshch. Khim., 2001, vol. 71, no. 4, pp. 600–609.
US Patent 7294211.
Freidlin, G.N., Alifaticheskie dikarbonovye kisloty (Aliphatic Dicarboxylic Acids), Moscow: Khimiya, 1978.
Gunawardena, N.R. and Brill, T.B., J. Phys. Chem. A, 2001, vol. 105, no. 10, pp. 1876–1881.
Kröger, C.F. and Freiberg, W., Z. Chem., 1969, vol. 5, no. 10, pp. 381–382.
Voronkov, M.G., Kashik, T.V., Makarskii, V.V., et al., Dokl. Akad. Nauk SSSR, 1976, vol. 227, no. 5, pp. 1116–1119.
Albert, A. and Serjeant, E., Ionization Constants of Acids and Bases. A Laboratory Manual, New York: Wiley, 1962.
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Original Russian Text © V.M. Chernyshev, A.V. Chernysheva, V.A. Taranushich, 2009, published in Zhurnal Prikladnoi Khimii, 2009, Vol. 82, No. 2, pp. 282–287.
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Chernyshev, V.M., Chernysheva, A.V. & Taranushich, V.A. Optimization of the synthesis of 5-amino-1,2,4-triazol-3-ylacetic acid and bis(5-amino-1,2,4-triazol-3-yl)methane. Russ J Appl Chem 82, 276–281 (2009). https://doi.org/10.1134/S1070427209020219
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DOI: https://doi.org/10.1134/S1070427209020219