Convenient and Environment-Friendly Synthesis of Sulfonyl Chlorides from S-Alkylisothiourea Salts via N-Chlorosuccinimide Chlorosulfonation
Convenient and Environment-Friendly Synthesis of Sulfonyl Chlorides from S-Alkylisothiourea Salts via N-Chlorosuccinimide Chlorosulfonation
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N-氯代琥珀酰亚胺氯磺化法以S-烷基异硫脲盐方便环保合成磺酰氯
DOI：
10.1055/s-0033-1338743
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发表时间：
2013-06-01
影响因子：
2.6
通讯作者：
Xu, Jiaxi
中科院分区：
文献类型：
--
作者：
Yang, Zhanhui;Xu, Jiaxi
开发了一种简便、实用、环保的磺酰氯合成方法。通过N-氯代丁二酰亚胺氯磺化，从易得的卤代烷或甲磺酸盐和廉价的硫脲合成了结构多样的S-烷基异硫脲盐，以中等到很好的产率合成了结构多样的磺酰氯。在大规模合成中，从废水中产生的副产物丁二酰亚胺可以方便地转化为起始剂N-氯代丁二酰亚胺，并与次氯酸钠(漂白剂)一起使用，使该方法可持续发展。
A convenient, practical, and environmentally friendly method for the synthesis of sulfonyl chlorides has been developed. Structurally diverse sulfonyl chlorides were synthesized in moderate to excellent yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea, via N-chlorosuccinimide chlorosulfonation. In large-scale syntheses, the byproduct succinimide from ‘waste water’ can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite (bleach) to make the method sustainable.