Abstract
Antipyrine and its benzenesulfonate were iodinated by solid-state mechanical activation (in the absence of solvent) under the action of iodine, iodine chloride, Me4N+ICl2 −, and Et4N+ICl2 − with the formation of 4-iodoantipyrine. The proposed process does not require organic solvents and meets all Green Chemistry demands. The best results were achieved with the use of tetraalkylammonium salts Me4N+ICl2 − and Et4N+ICl2 −.
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A. N. Evstropov, V. E. Yavorovskaya, E. S. Vorob’ev, et al., Khim.-Farm. Zh., 26(5), 50–53 (1992).
M. A. Trivedi and J. Labelled, Compd. Radiopharm., 38(5), 489–496 (1996).
RF Patent No. 2106344 (1998); Ref. Zh. Khim., 19O69P (1998).
RF Patent No. 2179551 (2002); Ref. Zh. Khim., 19O53P (2002).
M. Spacek, Chem. Prum., 34(5), 256–258 (1984).
L. M. Kustov and I. P. Begletskaya, Ross. Khim. Zh., 48(6), 3–12 (2004).
A. R. Hajipour, M. Arbabian, and A. E. Ruoho, J. Org. Chem., 67, 8622–8624 (2002).
V. M. Alexander, A. C. Khandekar, and S. D. Samant, Synlett., 12, 1895–1897 (2003).
E. A. Krasnokutskaya, Yu. A. Lesina, D. A. Gorlushko, and V. D. Filimonov, Zh. Org. Khim., 41, 876–880 (2005).
D. V. Kosynkin and J. M. Tour, Org. Lett., 3(7), 991–992 (2001).
A Chemist’s Handbook [in Russian], B. Nikol’skii (ed.), Goskhimizdat, Leningrad (1963), p. 1168.
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 41, No. 3, pp. 35–36, March, 2007.
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Krasnokutskaya, E.A., Trusova, M.E., Gibert, N.S. et al. 4-Iodoantipyrine synthesized by means of solid-state mechanical activation. Pharm Chem J 41, 154–156 (2007). https://doi.org/10.1007/s11094-007-0034-1
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DOI: https://doi.org/10.1007/s11094-007-0034-1