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Ultrafast synthesis of 2-(benzhydrylthio)benzo[d]oxazole, an antimalarial drug, via an unstable lithium thiolate intermediate in a capillary microreactor

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Abstract

We present an ultrafast approach for the synthesis of 2-(benzhydrylthio)benzo[d]oxazole, an antimalarial drug, in 75% yield from benzo[d]oxazole-2-thiol and benzhydryl bromide via an unstable lithium thiolate intermediate in the presence of n-BuLi. The precisely controlled two-step reaction at room temperature in a simple capillary microreactor enables a drastic decrease of the synthesis time to milliseconds (580 ms) from 10 min in a flask. Furthermore, a simple continuous-flow operation of the low cost reactor readily realizes a high throughput, leading to a several gram scale production (approximately 4 g per 13.3 min) at a very high flow rate of 7.6 ml min−1.

Graphical abstract: Ultrafast synthesis of 2-(benzhydrylthio)benzo[d]oxazole, an antimalarial drug, via an unstable lithium thiolate intermediate in a capillary microreactor

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Article information


Submitted
03 Feb 2020
Accepted
09 Mar 2020
First published
09 Mar 2020

React. Chem. Eng., 2020, Advance Article
Article type
Communication

Ultrafast synthesis of 2-(benzhydrylthio)benzo[d]oxazole, an antimalarial drug, via an unstable lithium thiolate intermediate in a capillary microreactor

B. T. Ramanjaneyulu, S. Vidyacharan, G. Ahn and D. Kim, React. Chem. Eng., 2020, Advance Article , DOI: 10.1039/D0RE00038H

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