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Received October 2, 2002
Accepted November 14, 2002
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Convenient Synthesis of N-Methylpyrrolidine-2-thione and Some Thioamides
Department of Applied Chemistry, School of Chemical Engineering, China University of Mining and Technology, Xuzhou 221008, Jiangsu, China 1Advanced Chemical Technology Division, Korea Research Institute of Chemical Technology, P.O. Box 107, Yusung, Daejeon 305-600, Korea
Korean Journal of Chemical Engineering, March 2003, 20(2),
10.1007/BF02697234
10.1007/BF02697234
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Abstract
The synthesis of thioamides and thiolactams, which are used as important organic intermediates, has attracted great attention. However, expensive reagents, severe reaction conditions and low yields of the target products made conventional methods inconvenient and economically infeasible. To overcome these disadvantages, we investigated a new process for synthesizing thioamides and thiolactams. We examined thermal reactions of CS2 with N-methyl-2-pyrrolidinone, formylamide, acetamide and N,N-dimethylformylamide, respectively. The results show that under optimum conditions N-methylpyrrolidine-2-thione and the corresponding thioamides can be obtained in good to excellent yields by the above thionation reactions.
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Eastman AD, Johnson MM, Skinner RD, U.S. Patent, 4,956,476 (1990)
Gronowitz S, Hornfeldt AB, Temciuc M, Synthesis, 483 (1993)
Harpp DN, MacDonald JG, Tetrahedron Lett., 24, 4927 (1983)
Hurd RN, DeLamater G, Chem. Rev., 61, 45 (1961)
Iino M, Kumagai J, Ito O, J. Fuel Soc. Jpn., 64, 210 (1985)
Ilankumaran P, Ramesha AR, Chandrasekaran S, Tetrahedron Lett., 36, 8311 (1995)
Lubosch W, Seebach D, Helv. Chim. Acta, 63, 102 (1980)
OOgata H, Tanaka Y, Oomura M, Ogata H, Orukawa A, Suzuki H, Jpn. Kokai Tokkyo Koho, Japan Patent, 08157450 (1996)
Olsson R, Hansen HC, Andersson CM, Tetrahedron Lett., 41, 7947 (2000)
Raucher S, Klein P, J. Org. Chem., 46, 3558 (1981)
Rechberger P, Gritzner G, Inorg. Chim. Acta, 31, 125 (1978)
Rohaly J, Novak L, Szantay C, Org. Prep. Proc. Int., 31, 693 (1999)
Sakamoto M, Takahashi M, Kamiya K, Yamaguchi K, Fujita T, Watanabe S, J. Am. Chem. Soc., 118(43), 10664 (1996)
Senyel M, Kurkcuoglu GS, J. Appl. Spectros., 68, 862 (2001)
Thomsen I, Clausen K, Scheibye S, Lawesson SO, Org. Synth., 62, 158 (1984)
Williams EL, U.S. Patent, 5,284,974 (1994)
Xie MQ, Lightner DA, J. Heterocyclic Chem., 28, 1753 (1991)
Yamaguchi H, Ushizawa N, Shimomura T, Jpn. Kokai Tokkyo Koho, Japan Patent, 61173139 (1986)
