Pharmacology, pharmacogenomics, drug discovery and design, drug therapy
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.
