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Molecules
Volume 29
Issue 23
10.3390/molecules29235496
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Article

Detailed Studies on the Methoxylation and Subsequent Dealkylation of N,N-Diethylbenzenesulfonamide Using a Tailor-Made Electrosynthetic Reactor

by
Ernák F. Várda
1,
Imre Gyűjtő
1,2,
Ferenc Ender
3,4,
Richárd Csekő
3,4,
György T. Balogh
1,5,6,* and
Balázs Volk
1,2,*
1
Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, Műegyetem rakpart 3, H-1111 Budapest, Hungary
2
Egis Pharmaceuticals Plc., Directorate of Drug Substance Development, P.O. Box 100, H-1475 Budapest, Hungary
3
Department of Electron Devices, Budapest University of Technology and Economics, Műegyetem rakpart 3, H-1111 Budapest, Hungary
4
Spinsplit Research and Development Ltd., Szőlőskert u. 0182/135, H-2220 Vecsés, Hungary
5
Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre út 9, H-1092 Budapest, Hungary
6
Center for Pharmacology and Drug Research & Development, Department of Pharmaceutical Chemistry, Semmelweis University, H-1085 Budapest, Hungary
*
Authors to whom correspondence should be addressed.
Molecules 2024, 29(23), 5496; https://doi.org/10.3390/molecules29235496
Submission received: 4 October 2024 / Revised: 11 November 2024 / Accepted: 12 November 2024 / Published: 21 November 2024
(This article belongs to the Special Issue Novel Studies of Organic Electrosynthesis)
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Abstract

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 N,N-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 N-methoxyalkyl intermediate, a precursor of the reactive and versatile N-sulfonyliminium cation, possible.
Keywords: electrochemistry; Shono oxidation; anodic oxidation; benzenesulfonamides; methoxylation; dealkylation electrochemistry; Shono oxidation; anodic oxidation; benzenesulfonamides; methoxylation; dealkylation

Share and Cite

MDPI and ACS Style

Várda, E.F.; Gyűjtő, I.; Ender, F.; Csekő, R.; Balogh, G.T.; Volk, B. Detailed Studies on the Methoxylation and Subsequent Dealkylation of N,N-Diethylbenzenesulfonamide Using a Tailor-Made Electrosynthetic Reactor. Molecules 2024, 29, 5496. https://doi.org/10.3390/molecules29235496

AMA Style

Várda EF, Gyűjtő I, Ender F, Csekő R, Balogh GT, Volk B. Detailed Studies on the Methoxylation and Subsequent Dealkylation of N,N-Diethylbenzenesulfonamide Using a Tailor-Made Electrosynthetic Reactor. Molecules. 2024; 29(23):5496. https://doi.org/10.3390/molecules29235496

Chicago/Turabian Style

Várda, Ernák F., Imre Gyűjtő, Ferenc Ender, Richárd Csekő, György T. Balogh, and Balázs Volk. 2024. "Detailed Studies on the Methoxylation and Subsequent Dealkylation of N,N-Diethylbenzenesulfonamide Using a Tailor-Made Electrosynthetic Reactor" Molecules 29, no. 23: 5496. https://doi.org/10.3390/molecules29235496

APA Style

Várda, E. F., Gyűjtő, I., Ender, F., Csekő, R., Balogh, G. T., & Volk, B. (2024). Detailed Studies on the Methoxylation and Subsequent Dealkylation of N,N-Diethylbenzenesulfonamide Using a Tailor-Made Electrosynthetic Reactor. Molecules, 29(23), 5496. https://doi.org/10.3390/molecules29235496

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