Issue
Korean Journal of Chemical Engineering,
Vol.20, No.2, 235-238, 2003
Convenient Synthesis of N-Methylpyrrolidine-2-thione and Some Thioamides
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.
[References]
  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