410
CHORNOUS et al.
2. Reaktsii
thiocyanate, and the mixture was stirred for 6 h under
reflux. It was then cooled, the precipitate of lead(II)
chloride was filtered off, the filtrate was evaporated,
and the residue was purified by recrystallization.
b. To a solution of 0.01 mol of chloride Ia Ij in
50 ml of anhydrous acetone we added 0.01 mol of
sodium thiocyanate, and the mixture was stirred for
4 h at room temperature. The precipitate of sodium
chloride was filtered off, the filtrate was evaporated,
and the residue was purified by recrystallization.
i metody issledovaniya organicheskikh
soedinenii (Reactions and Methods of Investigation
of Organic Compounds), Kazanskii, B.A., Knu-
nyants, I.L., Shemyakin, M.M., and Mel’nikov, N.N.,
Moscow: Khimiya, 1971, vol. 25, pp. 166 353.
3. Douglass, J.B. and Forman, L.E., J. Am. Chem. Soc.,
1934, vol. 56, no. 3, pp. 719 721.
4. Nazarova, Z.I. and Gakh, L.G., Zh. Obshch. Khim.,
1962, vol. 32, no. 8, pp. 2548 2551.
5. Gakh, I.G. and Nazarova, Z.I., Zh. Obshch. Khim.,
N-[3-Aryl(heteryl)-1-phenyl-4-pyrazolecarbonyl]-
thioureas IVa IVl (Table 2). a. To a solution of
0.005 mol of isothiocyanate IIa, IIb, IId, IIe, IIg, or
IIj in 25 ml of benzene we added 0.005 mol of amine
IIIa IIIh, and the mixture was heated for 2 h under
reflux. The solvent was evaporated, and the residue
was purified by recrystallization.
b. To a solution of 0.005 mol of chloride Ia, Ig, or
Ij in 20 ml of methylene chloride we added 0.005 mol
of ammonium thiocyanate and 0.1 g of PEG-600
poly(ethylene glycol), and the mixture was stirred
for 3 h at room temperature. Amine IIIb IIIg or
IIIh, 0.005 mol, was then added, and the mixture was
stirred for an additional 3 h. The solvent was removed,
and the precipitate was washed with 15 ml of water,
dried, and recrystallized.
N-(3-Aryl-1-phenyl-4-pyrazolecarbonyl)thio-
semicarbazides VIa VIj (Table 3). To a solution of
0.002 mol of isothiocyanate IIa, IIe, or IIg in 10 ml
of acetonitrile we added 0.002 mol of hydrazine
Va Vc, hydrazide Vd, or thiosemicarbazide Ve, and
the mixture was heated for 3 h under reflux. The
solvent was removed, and the precipitate was washed
with 15 ml of ethanol and recrystallized.
1966, vol. 36, no. 7, pp. 2183 2186.
6. Douglass, J.B. and Forman, L.E., J. Am. Chem. Soc.,
1934, vol. 56, no. 7, p. 1609.
7. Kaufmann, H.P. and Luthje, K., Arch. Pharm., 1960,
vol. 293, pp. 150 153.
8. Zhang, Y. and Wei, T., and Wand, L., Synth. Com-
mun., 1997, vol. 27, no. 5, pp. 751 756.
9. Zhang, Y., Wei, T., and Lu, J., Synth. Commun.,
1998, vol. 28, no. 5, pp. 3243 3248.
10. Czech. Patent no. 245088, 1985; Chem. Abstr., 1989,
vol. 110, no. 7876p.
11. Kumar, P., Srivastava, S.K., and Ramrahyani, A.K.,
Acta Sci. Ind. Chem., 1992, vol. 8, no. 4, pp. 208
210; Chem. Abstr., 1998, vol. 128, no. 22856x.
12. Uppol, K.S. and Banerji, S.K., Indian J. Agric.
Chem., 1985, vol. 18, no. 1, pp. 85 91; Chem. Abstr.,
1986, vol. 105, no. 37398y.
13. Liu, Ch., Zhang, L., Liu, W., and Zhang, H.,
Huanxue Yanjin Yu Yingyond, 1997, vol. 9, no. 5,
pp. 497 499; Chem. Abstr., 1998, vol. 128,
no. 22856x.
14. JPN Patent no. 09-301974, 1998; Chem. Abstr.,
1998, vol. 128, no. 22908r.
15. JPN Patent no. 09-132567, 1997; Chem. Abstr.,
REFERENCES
1997, vol. 127, no. 5086h.
1. Vovk, M.V., Mel’nichenko, N.V., Chornous, V.A.,
and Bratenko, M.K., Russ. J. Org. Chem., 2001,
vol. 37, no. 12, pp. 1747 1752.
16. Bratenko, M.K., Chornous, V.A., and Vovk, M.V.,
Russ. J. Org. Chem., 2001, vol. 37, no. 4, pp. 552
555.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 3 2002