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Development of an Efficient and Sustainable Synthesis of 2-(3-Methyl-1H-1,2,4-Triazol-1-Yl) Acetic Acid Under Continuous-Flow Conditions

preprint
submitted on 19.02.2020 and posted on 20.02.2020 by Simone Tortoioli, Astrid Friedli, Alice Prud’homme, Sylvia Richard-Bildstein, Philipp Kohler, Stefan Abele, Gianvito Vilé
A novel, metal-free process for the challenging synthesis of 2-(3-methyl-1H-1,2,4-triazol-1-yl) acetic acid (1) is reported, which features an efficient condensation for the triazole build-up under flow conditions. This continuous, two-step method is atom economical, highly selective and environmentally benign, due to the avoidance of chromatography and isolation steps. Compared to the earlier batch synthetic routes, higher yields were achieved in a flow reactor. In addition, a highly energetic intermediate could be controlled and handled in a safe manner. To generalize the established route, several triazoles were finally prepared under the described conditions, confirming that the methodology could find useful applications for the rapid and sustainable construction of differentially functionalized 1,2,4-triazoles.

History

Email Address of Submitting Author

gianvito.vile@polimi.it

Institution

Politecnico di Milano

Country

Italy

ORCID For Submitting Author

0000-0003-0641-8590

Declaration of Conflict of Interest

Nothing to declare.

Version Notes

Submitted: 16-Dec-2019. Revised: 12-Feb-2020.

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