Várda Ernák F, Gyűjtő Imre, Ender Ferenc, Csekő Richárd, Balogh György T, Volk Balázs
Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, Műegyetem rakpart 3, H-1111 Budapest, Hungary.
Egis Pharmaceuticals Plc., Directorate of Drug Substance Development, P.O. Box 100, H-1475 Budapest, Hungary.
Molecules. 2024 Nov 21;29(23):5496. doi: 10.3390/molecules29235496.
Benzenesulfonamides are an outstandingly important family of compounds in organic and medicinal chemistry. Herein, we report detailed studies on the electrochemical mono- and dideethylation of model compound -diethylbenzenesulfonamide. In this context, all parameters of the electrosynthesis were systematically investigated, with a special emphasis on solvent screening and the effect of water on the outcome of the reaction. Beside a commercially available electrochemical reactor, a custom-made device has also successfully been designed and used in these transformations. Optimization of the reaction led to a green, scaled-up synthesis of the dealkylated products. Our experiments also render the synthesis and potential in situ use of the corresponding -methoxyalkyl intermediate, a precursor of the reactive and versatile -sulfonyliminium cation, possible.
苯磺酰胺是有机化学和药物化学中一类极其重要的化合物。在此，我们报告了对模型化合物——二乙基苯磺酰胺的电化学单脱乙基化和双脱乙基化的详细研究。在此背景下，系统研究了电合成的所有参数，特别着重于溶剂筛选以及水对反应结果的影响。除了市售的电化学反应器外，还成功设计了一种定制装置并用于这些转化反应。反应的优化实现了脱烷基产物的绿色、放大合成。我们的实验还使得相应的甲氧基烷基中间体（一种活性且通用的磺酰亚胺阳离子的前体）的合成及潜在的原位使用成为可能。
