Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 17, Issue -, Pages 805-812Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.17.69
Keywords
chromatography-free; Lawesson?s reagent; scale-up; thioamide; thionation
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Funding
- National Natural Science Foundations of China [21972125, 21773210]
- Fundamental Research Funds for the Provincial Universities of Zhejiang [RFB2019005]
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Ethanol was found to be effective in decomposing the byproduct of Lawesson's reagent, facilitating the preparation of thioamides. A convenient process using ethylene glycol instead of ethanol for post-reaction workup was successfully developed, reducing environmental pollution and offering the opportunity for large-scale thio-substitution reactions.
After completing the thio-substitution with Lawesson?s reagent, ethanol was found to be effective in the decomposition of the inherent stoichiometric six-membered-ring byproduct from the Lawesson?s reagent to a highly polarized diethyl thiophosphonate. The treatment significantly simplified the following chromatography 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 a traditional phase separation, extraction, and recrystallization. The newly developed chromatography-free procedure did not generate P-containing aqueous waste, and only organic effluents were discharged. It is believed that the optimized procedure offers the great opportunity of applying the Lawesson?s reagent for various thio-substitution reactions on a large scale.
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