Detailed Studies on the Methoxylation and Subsequent Dealkylation of N,N-Diethylbenzenesulfonamide Using a Tailor-Made Electrosynthetic Reactor
Year: 2024
Type: article
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.
Source: Molecules
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $3,069
OpenAlex ID: W4404594926