Scale-up and optimization of a continuous flow synthesis of an α-thio-βchloroacrylamide

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Dennehy, Olga C.
Lynch, Denis
Collins, Stuart G.
Maguire, Anita R.
Moynihan, Humphrey A.
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Use of continuous flow processing to undertake a multistep chlorination cascade has been achieved with effective inline work-up and end-of-line crystallization in batch leading to isolation of α-thio-β-chloroacrylamide Z-3 in pure form from a complex reaction mixture, exploiting the advantage of efficient heat transfer in flow. During the development of a continuous flow strategy for the production of appreciable quantities of the α-thio-β-chloroacrylamides, difficulties surrounding a labour and resource intensive work-up followed by final product isolation were addressed. A greener solvent choice was applied to the chemical synthesis which enabled inline purification and separation, resulting in the crystallization of pure product directly from the reaction mixture. This process was readily scalable and demonstrated control over impurity formation and removal, which is key in an industrial setting.
Continuous processing , Flow chemistry , Process impurities , α-thio-βchloroacrylamides
Dennehy, O. C., Lynch, D., Collins, S. G., Maguire, A. R. and Moynihan, H. A. (2020) ‘Scale-up and optimization of a continuous flow synthesis of an α-thio-β-chloroacrylamide’, Organic Process Research and Development. doi: 10.1021/acs.oprd.0c00079
© 2020, American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Process Research and Development after technical editing by the publisher. To access the final edited and published work see