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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
Reaction Chemistry & Engineering ( IF 3.9 ) Pub Date : 2020-03-09 , DOI: 10.1039/d0re00038h
Bandaru T. Ramanjaneyulu 1, 2, 3, 4, 5 , Shinde Vidyacharan 1, 2, 3, 4, 5 , Gwang-Noh Ahn 1, 2, 3, 4, 5 , Dong-Pyo Kim 1, 2, 3, 4, 5
Affiliation  

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.

中文翻译:

通过毛细管微反应器中不稳定的硫醇锂中间体超快速合成抗疟药2-(苯甲硫基)苯并[d]恶唑

我们提出了一种通过存在下的不稳定的硫醇锂中间体从苯并[ d ]恶唑-2-硫醇和苄基溴化物以75%的产率合成抗疟药2-(苯甲硫基)苯并[ d ]恶唑的超快方法。的n -BuLi。在简单的毛细管微反应器中,在室温下进行精确控制的两步反应可将合成时间从烧瓶中的10分钟急剧减少至毫秒(580 ms)。此外,低成本反应器的简单连续流操作容易实现高产量,从而以7.6 ml min -1的非常高的流速导致几克规模的产量(每13.3分钟约4 g)。
更新日期:2020-03-09
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