A new industrial process for 10-methoxyiminostilbene: Key intermediate for the synthesis of oxcarbazepine

Organic Process Research and Development

Volumn 13, Issue 5, 2009, Pages 870-874

  Singh, Harnam ^a   Gupta, Nitin ^a   Kumar, Pramod ^a   Dubey, Sushil K ^a   Sharma, Pawan K ^b  

^a Jubilant Organosys   (India)

^b KURUKSHETRA UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 70449440878     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op900127v     Document Type: Article

References (42)

1. Ambrosio, A. F.; Soares-da-Silva, P.; Carvalho, C. M.; Carvalho, A. P. Neurochem. Res. 2002, 27, 121-130
2. Vajda, F. J. E. J. Clin. Neurosci. 2008, 7,88.
3. Gomez-Arguelles, J. M.; Dorado, R.; Sepulveda, J. M.; Huet, R.; Arrojo, F. G.; Aragon, E.; Herrera, A.; Trron, C.; Anciones, B. J. Clin. Neurosci. 2008, 15, 516.
4. Boireau, A.; Bordier, F.; Doble, A.; Dubedat, P.; Louvel, E.; Meunier, M.; Miquet, J.-M.; Tutzmann, J.-M. U.S. Patent 5,658,900, 1997.
5. Lertratanangkoon, K.; Honing, M. G. Drug Metab. Disvos. 1982, 10, 1.
6. Clemens, B.; Menes, A.; Nagy, Z. Acta Neurol. Scand. 2004, 109, 324.
7. Schindler, W. U.S. Patent 2,948,718, 1960.
8. Vyas, D. K.; Jafri, S. W.; Kulkarni, K. A. U.S. Patent 6, 245, 908, 2001.
9. Eckardt, R.; Janch, J. H. U.S. Patent 7,015,322, 2006.
10. Schramek, H.; Riethmann, J.; Kllen, J. Swiss Patent 442319, 1968.
11. Craig, P. N.; Lester, B. M.; Saggiomo, A. J.; Kaiser, C.; Zirker, C. L. J. Org. Chem. 1961, 26, 135.
12. Knell, A.; Monti, D.; Maciejewski, M.; Baiker, A. Avvl. Catal. 1995, 121, 139.
13. a) Lapworth, A. J. Chem. Soc. 1901, 79, 126.
14. b) Craig, P. N. U.S. Patent 3,074,931, 1963;
15. Chem. Abstr. 1963, 59, P3900f.
16. a) Fuenfschilling, P. C.; Zaugg, W.; Beutler, U.; Kaufmann, D.; Lohse, O.; Mutz, J. P.; Onken, U.; Reber, J. L.; Shenton, D. Org. Process Res. Dev. 2005, 9, 272.
17. b) Carril, M.; San, M. R.; Churruca, F.; Tellitu, I.; Dominguez, E. Org. Lett. 2005, 7, 4787.
18. c) Lohse, O.; Beutler, U.; Funfeschilling, P.; Furel, P.; Julien, F.; Kaufmann, D.; Penn, G.; Zaugg, W. Tetrahedron Lett. 2001, 42, 385.
19. d) Ernst, A. European Patent 0028028, 1981.
20. e) Gosteli, J. Swiss Patent 642950, 1984.
21. f) Miller, L.; Ellinwood, A. E. U.S. Patent 3, 642, 775, 1972.
22. g) Heckendorn, R.; Zergenyi, J.; Menard, F. Canadian Patent 1112241, 1981.
23. a) Manadakini, M.; Muthukumaran, N.; Thennati, R. WO 2005/ 096709, 2005.
24. b) Aufderhaar, K. E.; Sprecher, B. K.; Zergenyi, S. J. U.S. Patent 4,436,660, 1984.
25. c) Aufderhaar, K. E. U.S. Patent 4,452,738, 1984.
26. d) Aufderhaar, K. E. U.S. Patent 4, 540, 514, 1985.
27. e) Aufderhaar, K. E. U.S. Patent 4, 559, 174, 1985.
28. f) Aufderhaar, K. E. U.S. Patent 4,579,683, 1986.
29. g) Banti, M. A.; Bollini, R. D.; Lombardia, R.; Serra, C. M. U.S. Patent 2007/0149507, 2007.
30. Lohse, O.; Beutler, U.; Funfschilling, P.; Furet, P.; France, J.; Kauffmann, D.; Penn, G.; Zaugg, W. Tetrahedron Lett. 2001, 42, 385.
31. Kauffmann, D.; Funfschilling, P.; Beutler, U.; Hoehn, P.; Lohse, O.; Zaugg, W. Tetrahedron Lett. 2004, 45, 5275.
32. Funfschilling, P.; Kauffmann, D.; Lohse, O.; Beutler, U.; Zaugg, W. Chem. Abstr. 2001, 135, 166785. WO 01/56992, 2001.
33. a) Parenky, C.; Chaturvedi, R. U.S. Patent, 10, 032, 647, 2007.
34. b) Gutman, D.; Baidossi, W. U.S. Patent 2006/0241293, 2006.
35. c) Sivakumar, B. V.; Bhirud, S. B.; Batchu, C.; Kale, S. A. U.S. Patent 7, 459, 553, 2008.
36. d) Milanese, A. WO 118550, 2005.
37. e) Gupta, N.; Singh, H.; Kumar, P.; Dubey, S. K. WO 141798, 2007.
38. Alam, A.; Takaguchi, Y.; Tsuboi, S. J. Fac. Environ. Sci.Technol. 2005, 10, 105;
39. Chem. Abstr. 2005, 142, 409887.
40. Chassaing, C.; Haudrechy, A.; Langlois, Y. Tetrahedron Lett. 1997, 38, 4415.
41. The only byproduct at this stage is 5, 5-dimethylhydantoin. Efforts were made to recover 5,5-dimethylhydantoin from the resulting filtrate. The filtrate is distilled to remove methanol, the resulting concentrate is dissolved in water (5 volumes) at 30-35 °C and extracted with dichloromethane (2 × 1.5 volumes). The aqueous phase is partially distilled (2 volumes), and the residual aqueous layer is cooled to 10-15 °C when a solid starts separating out. Filtration of the slurry affords 5, 5-dimethylhydantoin in 50-60% yield.
42. Charles, C. P.; Joseph, M. Org. Synth. 1965, 45, 22.