Detailed Studies on the Methoxylation and Subsequent Dealkylation of <i>N,N</i>-Diethylbenzenesulfonamide Using a Tailor-Made Electrosynthetic Reactor
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 <i>N,N</i>-diethylbenzenesulfonamide. In this context, all parameters of the ele...
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| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-11-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/29/23/5496 |
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| Summary: | 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 <i>N,N</i>-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 <i>N</i>-methoxyalkyl intermediate, a precursor of the reactive and versatile <i>N</i>-sulfonyliminium cation, possible. |
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| ISSN: | 1420-3049 |