A Convenient Synthesis of N-Functionalized Perfluoroalkanesulfonamides

This article describes the synthesis of new N-functionalized perfluoroalkanesulfonamides (5) with two sulfonamides functionalities. Perfluoroalkanesulfonyl fluoride underwent a reaction with 2-chloroethylamine hydrochloride or 3-bromopropylamine hydrobromide to give N-(2-chloroethyl or 3-bromopropyl) perfluoroalkanesulfonamides (1). Reaction of (1) with potassium thiocyanate gave N-(2-thiocyanatoethyl or 3-thiocyanatopropyl) perfluoroalkanesulfonamides (3). The sulfonyl chloride derivatives (4) were prepared by reaction of 3 with sulfuryl chloride. In the last step, 4 reacted with ammonia to give the bis sulfonamides derivatives (5). The structures of all new compounds prepared were determined by ¹H, ¹⁹F, and ¹³C NMR spectroscopies and by HR-MS.