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31.9.2.1.4.8.1 Variation 1: N-Alkylation with Alkyl Halides

DOI: 10.1055/sos-SD-031-00644

Shcherbakova, I.Science of Synthesis, (200731817.

Arenesulfonamides such as 142 are relatively strong NH acids and are effectively alkylated under liquidliquid or solidliquid phase-transfer-catalysis conditions (e.g., to give 143, Scheme 61).[‌180‌] Regardless of the sulfonamide/alkyl bromide molar ratio, only dialkylation is observed and the reaction cannot be carried out stepwise with the formation of N-monoalkylarenesulfonamides.

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