Convenient Synthesis of N-Methylpyrrolidine-2-thione and Some Thioamides

Zhi-Min Zong; Yao-Li Peng; Zhi-Gang Liu; Shi-Lu Zhou; Lin Wu; Xiao-Hua Wang; Xian-Yong Wei; Chul Wee Lee

Korean Journal of Chemical Engineering, Vol.20, No.2, 235-238, March, 2003

DOI10.1007/BF02697234 Export Citation

Convenient Synthesis of N-Methylpyrrolidine-2-thione and Some Thioamides

Zhi-Min Zong, Yao-Li Peng, Zhi-Gang Liu, Shi-Lu Zhou, Lin Wu, Xiao-Hua Wang, Xian-Yong Wei^†, and Chul Wee Lee¹

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

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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.

Keywords:CS2;Amides;Thionation;N-Methylpyrrolidine-2-thione;Thioamides

[References]

Borthakur N, Goswami A, Tetrahedron Lett., 36, 6745 (1995)
Dunstan PO, Thermochim. Acta, 389(1-2), 25 (2002)
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)

[Related Articles]

[1] Borthakur N, Goswami A, Tetrahedron Lett., 36, 6745 (1995)

[2] Dunstan PO, Thermochim. Acta, 389(1-2), 25 (2002)

[3] Eastman AD, Johnson MM, Skinner RD, U.S. Patent, 4,956,476 (1990)

[4] Gronowitz S, Hornfeldt AB, Temciuc M, Synthesis, 483 (1993)

[5] Harpp DN, MacDonald JG, Tetrahedron Lett., 24, 4927 (1983)

[6] Hurd RN, DeLamater G, Chem. Rev., 61, 45 (1961)

[7] Iino M, Kumagai J, Ito O, J. Fuel Soc. Jpn., 64, 210 (1985)

[8] Ilankumaran P, Ramesha AR, Chandrasekaran S, Tetrahedron Lett., 36, 8311 (1995)

[9] Lubosch W, Seebach D, Helv. Chim. Acta, 63, 102 (1980)

[10] OOgata H, Tanaka Y, Oomura M, Ogata H, Orukawa A, Suzuki H, Jpn. Kokai Tokkyo Koho, Japan Patent, 08157450 (1996)

[11] Olsson R, Hansen HC, Andersson CM, Tetrahedron Lett., 41, 7947 (2000)

[12] Raucher S, Klein P, J. Org. Chem., 46, 3558 (1981)

[13] Rechberger P, Gritzner G, Inorg. Chim. Acta, 31, 125 (1978)

[14] Rohaly J, Novak L, Szantay C, Org. Prep. Proc. Int., 31, 693 (1999)

[15] Sakamoto M, Takahashi M, Kamiya K, Yamaguchi K, Fujita T, Watanabe S, J. Am. Chem. Soc., 118(43), 10664 (1996)

[16] Senyel M, Kurkcuoglu GS, J. Appl. Spectros., 68, 862 (2001)

[17] Thomsen I, Clausen K, Scheibye S, Lawesson SO, Org. Synth., 62, 158 (1984)

[18] Williams EL, U.S. Patent, 5,284,974 (1994)

[19] Xie MQ, Lightner DA, J. Heterocyclic Chem., 28, 1753 (1991)

[20] Yamaguchi H, Ushizawa N, Shimomura T, Jpn. Kokai Tokkyo Koho, Japan Patent, 61173139 (1986)