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Journal of the Iranian Chemical Society

, Volume 16, Issue 3, pp 501–509 | Cite as

An innovative and efficient method to synthesize meloxicam in one-step procedure with respect to the green chemistry

  • Pierrick Dufrénoy
  • Alina Ghinet
  • Marie Hechelski
  • Adam Daïch
  • Christophe WaterlotEmail author
Original Paper
  • 17 Downloads

Abstract

An improved procedure for the synthesis of meloxicam drug (methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazol-2-amine-3-carboxylate 1,1-dioxide) was described in one-step using mainly impregnated montmorillonite K10 (MK10) with ZnCl2 as a heterogeneous catalyst. This innovative method was compared to the last described procedure employed in the manufacture of this anti-inflammatory drug by means of some metrics used in a first step of the evaluation process of the environmental impact of a chemical transformation. Apart from the yield, which was 90%, atom economy, waste, environmental factor, reaction mass efficiency and stoichiometric factor were calculated as 91.6%, 8.4%, 0, 8.1% and 1%, respectively. Interpretation of these metrics was given and highlighted the fact that the strategy used in the current study may be considered as an environmental-friendly and sustainable method that fits well in the green chemistry concepts.

Keywords

Meloxicam Green chemistry Metrics Heterogeneous catalyst Montmorillonite K10 

Notes

Acknowledgements

The authors warmly thank Yncréa Hauts-de-France and the “Fondation de La Catho de Lille” for their financial support of this study in the frame of « Matériaux Verts Fonctionnels » program (P.D.’s and M. H.’s PhD scholarships). The authors are also grateful to the “Université Le Havre Normandie” for technical help.

References

  1. 1.
    R.S. Varma, Green Chem. 313, 43 (1999)CrossRefGoogle Scholar
  2. 2.
    P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 57, 9225 (2001)CrossRefGoogle Scholar
  3. 3.
    T.J. Mason, Chem. Soc. Rev. 26, 443 (1997)CrossRefGoogle Scholar
  4. 4.
    B. Banerjee, Ultrason. Sonochem. 35, 1 (2017)CrossRefGoogle Scholar
  5. 5.
    B. Banerjee, Ultrason. Sonochem. 35, 15 (2017)CrossRefGoogle Scholar
  6. 6.
    S.L. Barbosa, M.J. Dabdoub, G.R. Hurtado, S.I. Klein, A.C.M. Baroni, C. Cunha, Appl. Catal. A Gen.l 313, 146 (2006)CrossRefGoogle Scholar
  7. 7.
    H.M. Marvaniya, K.N. Modi, D.J. Sen, Int. J. Drug. Dev. Res. 3, 34 (2011)Google Scholar
  8. 8.
    A. McKillop, D.W. Young, Synthesis 6, 401 (1979)CrossRefGoogle Scholar
  9. 9.
    A. McKillop, D.W. Young, Synthesis 7, 481 (1979)CrossRefGoogle Scholar
  10. 10.
    B.M. Khadilkar, S.D. Borkar, Tetrahedron Lett. 38, 1641 (1997)CrossRefGoogle Scholar
  11. 11.
    M. Nikoorazm, Sci. Iran. 20, 603 (2013)Google Scholar
  12. 12.
    N.A. Noureldin, D.G. Lee, Tetrahedron Lett. 22, 4889 (1981)CrossRefGoogle Scholar
  13. 13.
    B. Chiche, A. Finiels, C. Gauthier, P. Geneste, J. Org. Chem. 51, 2128 (1986)CrossRefGoogle Scholar
  14. 14.
    V. Paul, A. Sudalai, T. Daniel, K.V. Srinivasan, Tetrahedron Lett. 35, 2601 (1994)CrossRefGoogle Scholar
  15. 15.
    B.M. Choudary, M.L. Kantam, M. Sateesh, K.K. Rao, P.L. Santhi, Appl. Catal. A Gen. 149, 257 (1997)CrossRefGoogle Scholar
  16. 16.
    V.R. Choudhary, S.K. Jana, N.S. Patil, Tetrahedron Lett. 43, 1105 (2002)CrossRefGoogle Scholar
  17. 17.
    K. Bachari, O. Cherifi, Appl. Catal. A Gen. 319, 259 (2007)CrossRefGoogle Scholar
  18. 18.
    S. Horike, M. Dincâ, K. Tamaki, J.R. Long, J. Am. Chem. Soc. 130, 5854 (2008)CrossRefGoogle Scholar
  19. 19.
    D.J. Upadhyaya, S.D. Samant, Appl. Catal. A Gen. 340, 42 (2008)CrossRefGoogle Scholar
  20. 20.
    N.T.S. Phan, K.K.A. Ly, T.D. Phan, Appl. Catal. A: Gen. 382, 246 (2010)CrossRefGoogle Scholar
  21. 21.
    X. Chagjiu, L. Min, Z. Bin, S. Xingtian, Sci. Res. 14, 7 (2012)Google Scholar
  22. 22.
    S.S. Patil, S.D. Jadhav, M.B. Deshmukh, Indian J. Chem. 52B, 1172 (2013)Google Scholar
  23. 23.
    T. Ennaert, J. Van Aelst, J. Dijkmans, R. De Clercq, W. Schutyser, M. Dusselier, D. Verboekend, B.F. Sels, Chem. Soc. Rev. 45, 584 (2016)CrossRefGoogle Scholar
  24. 24.
    O. Sieskind, P. Albrecht, Tetrahedron Lett. 34, 1197 (1993)CrossRefGoogle Scholar
  25. 25.
    Z.H. Zhang, T.S. Li, F. Yang, G.G. Fu, Synth. Commun. 28, 3105 (1998)CrossRefGoogle Scholar
  26. 26.
    T.S. Li, Z.H. Zhang, T.S. Jin, Synth. Commun. 29, 181 (1999)CrossRefGoogle Scholar
  27. 27.
    S.A.E. Ayoubi, F. Texier-Boullet, J. Chem. Res. (S) 1, 208 (1995)Google Scholar
  28. 28.
    R.S. Varma, Tetrahedron 58, 1235 (2002)CrossRefGoogle Scholar
  29. 29.
    G. Song, B. Wang, X. Bu, Y. Kang, Y.L. Yang, Synth. Commun. 35, 2875 (2005)CrossRefGoogle Scholar
  30. 30.
    S. Dasgupta, B Török, Org. Prep. Proced. Int. 40, 1 (2008)CrossRefGoogle Scholar
  31. 31.
    G. Nagendrappa, Appl. Clay Sci. 53, 106 (2011)CrossRefGoogle Scholar
  32. 32.
    M. Balogh, I. Hermecz, Z. Meszaros, P. Laszlo, Helv. Chim. Acta 27, 2270 (1984)CrossRefGoogle Scholar
  33. 33.
    A. Maquestiau, A. Mayence, J.J. Vanden, Eynde, Tetrahedron Lett. 32, 3839 (1991)CrossRefGoogle Scholar
  34. 34.
    P. Laszlo, P. Pennetreau, A. Krief, Tetrahedron Lett. 27, 3153 (1986)CrossRefGoogle Scholar
  35. 35.
    S. Chalais, A. Cornelis, P. Laszlo, A. Mathy, Tetrahedron Lett. 26, 2327 (1985)CrossRefGoogle Scholar
  36. 36.
    M. Balogh, A. Cornéli, P. Laszlo, Tetrahedron Lett. 25, 3313 (1984)CrossRefGoogle Scholar
  37. 37.
    C. Waterlot, D. Couturier, B. Hasiak, J. Chem. Res. 0417 (2000)Google Scholar
  38. 38.
    A. Cornelis, P. Laszlo, P. Pennetreau, Clay Miner. 18, 437 (1983)CrossRefGoogle Scholar
  39. 39.
    A. Cornelis, P. Laszlo, Synthesis 10, 849 (1980)CrossRefGoogle Scholar
  40. 40.
    A. Cornélis, A. Gerstmans, P. Laszlo, A. Mathy, I. Zieba, Catal. Lett. 6, 103 (1990)CrossRefGoogle Scholar
  41. 41.
    P.D. Clark, A. Kirk, R.A. Kydd, Catal. Lett. 25, 163 (1994)CrossRefGoogle Scholar
  42. 42.
    J.J. Vanden Eynde, A. Mayence, Y.V. Haverbecke, Tetrahedron Lett. 36, 3133 (1995)CrossRefGoogle Scholar
  43. 43.
    R. Varala, R. Enugala, S.R. Adapa, Arkivoc 13, 171 (2006)Google Scholar
  44. 44.
    G.D. Yadav, K.P. Pimparkar, J. Mol. Catal. A Chem 264, 179 (2007)CrossRefGoogle Scholar
  45. 45.
    A. Cornélis, P. Laszlo, S. Wang, Tetrahedron Lett. 34, 3849 (1993)CrossRefGoogle Scholar
  46. 46.
    C. Waterlot, D. Couturier, B. Rigo, A. Ghinet, M. De Backer, Chem. Pap. 6, 873 (2011)Google Scholar
  47. 47.
    A. Dhakshinamoorthy, K. Knagaraj, K. Pitchumani, Tetrahedron Lett. 52, 69 (2011)CrossRefGoogle Scholar
  48. 48.
    https://clinicaltrials.gov. Accessed 15 Nov 2017
  49. 49.
    M. Zia-ur-Rehman, J.A. Choudary, S. Ahmad, Bull. Korean Chem. Soc. 26, 1771 (2005)CrossRefGoogle Scholar
  50. 50.
    T. Mezei, N. Mesterházy, T. Bakó, M. Porcs-Makkay, G. Simig, B. Volk, Org. Proc. Res. Dev. 13, 567 (2009)CrossRefGoogle Scholar
  51. 51.
    B.M. Trost, Science 254, 1471 (1991)CrossRefGoogle Scholar
  52. 52.
    R.A. Sheldon, Green Chem. 9, 1273 (2007)CrossRefGoogle Scholar
  53. 53.
    A.D. Curzons, D.J.C. Constable, D.N. Mortimer, V.L. Cunningham, Green Chem. 3, 1 (2001)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  1. 1.Laboratoire de chimie durable et santéYncrea Hauts-de-France, HEILille CedexFrance
  2. 2.Faculté de médecine, Pôle rechercheInserm U995, LIRIC, Université de Lille, CHU de LilleLille CedexFrance
  3. 3.Faculty of Chemistry‘Alexandru Ioan Cuza’ University of IasiIasiRomania
  4. 4.Laboratoire Génie Civil et géoEnvironnement (LGCgE)Yncrea Hauts-de-FranceLille cedexFrance
  5. 5.Normandie Univ., UNILEHAVRE, FR 3038 CNRS, URCOM EA 3221, UFR Sciences & TechniquesLe Havre CedexFrance

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