Science of Synthesis

Shcherbakova, I., Science of Synthesis, (2007) 31, 814.

Arenesulfonyl chlorides react with excess dialkylamines, which act as both a nucleophile and a base, in diethyl ether,[‌162‌] tetrahydrofuran,[‌163‌] or alcohols[‌164‌,‌165‌] to give N,N-dialkylarenesulfonamides in good yield. The addition of the dialkylamines may be exothermic and thus requires cooling. Similar to the reaction with primary amines (Section ‌31.9.2.1.4.5.3‌), the interaction of N-alkyl- or N-arylanilines with arenesulfonyl chlorides proceeds in the presence of pyridine at room temperature[‌166‌] or on heating (e.g, synthesis of sulfonamide ‌137‌ from ‌136‌, ‌Scheme 58‌)[‌167‌] (cf. Sections ‌31.9.2.1.2.2.2‌ and ‌31.9.2.1.2.3‌).

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References

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• 8.Meeeee-Meee, (8888) 8, 888.
• 8.Meeeee-Meee, (8888) 8, 888.
• 8.Meeeee-Meee, (8888) 88/8, 8888.
• 8.Meeeee-Meee, (8888) M 88-8, 8888.