A Column-Free and Aqueous Waste-Free Process for Thioamide Preparation with Lawesson’s reagent

  1. Ke Wu,
  2. Yichen Ling,
  3. An Ding,
  4. Liqun JinORCID Logo,
  5. Nan Sun,
  6. Baoxiang Hu,
  7. Zhenlu Shen and
  8. Xinquan HuORCID Logo

Submitting author affiliation: Zhejiang University of Technology, Hangzhou, China

Beilstein Arch. 2020, 2020126. https://doi.org/10.3762/bxiv.2020.126.v1

Published 05 Nov 2020

  • Preprint

Abstract

After completing thio-substitution with the Lawesson’s reagent, ethanol was found to be able to efficiently decompose the inherent stoichiometric six-membered-ring by-product from the Lawesson’s reagent to a highly polarized diethyl thiophosphate. This treatment could significantly simplify the following column purification of the desired thioamide in a small scale preparation. As scaling up the preparation of two pincer-type thioamides, we have successfully developed a convenient process with ethylene glycol to replace ethanol during the workup, including traditional phase-cut, extraction, and re-crystallization. The newly developed column-free procedure did not generate P-contained aqueous waste, and only organic effluents were discharged. It was believed that the optimized procedure can greatly provide opportunity of the application of the Lawesson’s reagent for various thio-substituted reacions in scaling up preparation.

Keywords: Lawesson’s reagent; Column-free; Thionation; Thioamide; Scale-up

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Wu, K.; Ling, Y.; Ding, A.; Jin, L.; Sun, N.; Hu, B.; Shen, Z.; Hu, X. Beilstein Arch. 2020, 2020126. doi:10.3762/bxiv.2020.126.v1

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