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

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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.

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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.

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Authors and Affiliations

  1. Laboratoire de chimie durable et santé, Yncrea Hauts-de-France, HEI, 13 rue de Toul, 59046, Lille Cedex, France

    Pierrick Dufrénoy & Alina Ghinet

  2. Faculté de médecine, Pôle recherche, Inserm U995, LIRIC, Université de Lille, CHU de Lille, Place Verdun, 59045, Lille Cedex, France

    Pierrick Dufrénoy & Alina Ghinet

  3. Faculty of Chemistry, ‘Alexandru Ioan Cuza’ University of Iasi, Bd. Carol I nr. 11, 700506, Iasi, Romania

    Alina Ghinet

  4. Laboratoire Génie Civil et géoEnvironnement (LGCgE), Yncrea Hauts-de-France, 48 boulevard Vauban, 59046, Lille cedex, France

    Marie Hechelski & Christophe Waterlot

  5. Normandie Univ., UNILEHAVRE, FR 3038 CNRS, URCOM EA 3221, UFR Sciences & Techniques, 25 rue Philipe Lebon, BP: 1123, F-76063, Le Havre Cedex, France

    Pierrick Dufrénoy & Adam Daïch

Authors
  1. Pierrick Dufrénoy
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  2. Alina Ghinet
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  3. Marie Hechelski
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  5. Christophe Waterlot
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Correspondence to Christophe Waterlot.

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Dufrénoy, P., Ghinet, A., Hechelski, M. et al. An innovative and efficient method to synthesize meloxicam in one-step procedure with respect to the green chemistry. J IRAN CHEM SOC 16, 501–509 (2019). https://doi.org/10.1007/s13738-018-1525-6

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  • DOI: https://doi.org/10.1007/s13738-018-1525-6

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