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Vol. 29 No. 7 (2017): Vol 29 Issue 7

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Evaluation of Synthesis of Methyl 3-Chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate Using Green Metrics

https://doi.org/10.14233/ajchem.2017.20529
Rohidas Gilbile
Department of Chemistry, Pacific Academy of Higher Education and Research University, Udaipur-313 024, India; Green Evolution Laboratories, Wangapally Village, Nalgonda-500 085, India
Ram Bhavani
Green Evolution Laboratories, Wangapally Village, Nalgonda-500 085, India
Ritu Vyas
Department of Chemistry, Pacific Academy of Higher Education and Research University, Udaipur-313 024, India

Corresponding Author(s) : Rohidas Gilbile

rohidasgilbile2017@gmail.com

Asian Journal of Chemistry, Vol. 29 No. 7 (2017): Vol 29 Issue 7

Abstract

A modified synthesis of methyl 3-chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate (halosulphuron) is described. The merits of the synthesis are (i) one pot chlorination of methyl 1-methyl-1H-pyrazole-4-carboxylate (1) in presence of sulphuryl chloride resulting in methyl 3,5-dichloro-1-methyl-1H-pyrazole-4-carboxylate (2) (ii) conversion of 3-chloro-5-mercapto-1-methyl-1H-pyrazole-4-carboxylate (3) to 3-chloro-1-methyl-5-sulfamoyl pyrazole-4-carboxylate (4) under mild reaction conditions utilizing tetrabutyl ammonium chloride, N-chlorosuccinimide and ammonium carbonate (iii) condensation of sulphonamide (4) with carbamate (6) by microwave irradiation. Efforts were made to calculate, atom economy, reaction mass efficiency and E-factor for all the reaction steps involved in the synthesis of halosulfuron. The E-factor values in step 2 and step 4 reaction is lower, indicating that these reactions are greener (generation of less waste) when compared to the remaining steps in the synthesis.

Keywords

Halosulphuron Synthesis Sulphonylureas Atomic economy E-factor Green metrics
Gilbile, R., Bhavani, R., & Vyas, R. (2017). Evaluation of Synthesis of Methyl 3-Chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate Using Green Metrics. Asian Journal of Chemistry, 29(7), 1477–1481. https://doi.org/10.14233/ajchem.2017.20529
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