优化流动合成Z-α-硫-β-氯丙烯酰胺过程中杂质e异构体的形成E/Z在间歇和流动中的光异构化,以及两种异构体的固态表征

IF 3.1 3区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY
Olga C. Dennehy, Denis Lynch, U. B. Rao Khandavilli, Simon E. Lawrence, Stuart G. Collins, Anita R. Maguire and Humphrey A. Moynihan
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引用次数: 0

摘要

N-(4-甲基苯基)-Z-3-氯-2-(苯硫代)丙烯酰胺(Z-3)是一种有价值的反应底物,用于一系列合成转化,可以通过涉及批处理和流动方法的三步工艺获得。化合物Z-3作为一种高纯度的结晶材料被分离出来,然而,在Z-3材料的固体样品中发现e -异构体E-3在储存过程中形成。通过批处理和流动两种方式的光异构化,获得了E-3和纯分离样品的比例增加,且流动过程在处理时间上是最佳的。Z和E异构体的晶体结构分析强调了分子构象和超分子相互作用的关键差异,与Z-3相比,E-3的平面度偏差更大。用PXRD和DSC对不同溶剂重结晶后的Z-3样品进行分析,得到的数据与确定的Z-3晶体结构一致。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Formation of the E-isomer as an impurity in the optimized flow synthesis of a Z-α-thio-β-chloroacrylamide; E/Z photoisomerization in batch and flow, and solid state characterization of both isomers†

Formation of the E-isomer as an impurity in the optimized flow synthesis of a Z-α-thio-β-chloroacrylamide; E/Z photoisomerization in batch and flow, and solid state characterization of both isomers†

N-(4-Methylphenyl)-Z-3-chloro-2-(phenylthio)propenamide (Z-3), which is valuable as a reactive substrate for a range of synthetic transformations, can be obtained by a three-step process involving both batch and flow methodologies. Compound Z-3 was isolated as a crystalline material of high purity, however, the E-isomer, E-3, was found to form in solid samples of Z-3 material during storage. Increased ratios of E-3 and pure isolated samples were obtained by photoisomerization in batch and flow modes, with the flow process being optimal in terms of process time. Crystal structure analysis of both the Z and E isomers highlighted key differences in molecular conformations and supramolecular interactions with greater deviation from planarity evident in E-3 relative to Z-3. Analysis of samples of Z-3 by PXRD and DSC after recrystallization from a variety of solvents gave data consistent with the determined crystal structure of Z-3.

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来源期刊
Reaction Chemistry & Engineering
Reaction Chemistry & Engineering Chemistry-Chemistry (miscellaneous)
CiteScore
6.60
自引率
7.70%
发文量
227
期刊介绍: Reaction Chemistry & Engineering is a new journal reporting cutting edge research into all aspects of making molecules for the benefit of fundamental research, applied processes and wider society. From fundamental, molecular-level chemistry to large scale chemical production, Reaction Chemistry & Engineering brings together communities of chemists and chemical engineers working to ensure the crucial role of reaction chemistry in today’s world.
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