Abstract
Three-component condensation of trifluoromethanesulfonamide with paraformaldehyde and succinamide depending on the reaction conditions led alongside bis(trifluoromethanesulfonamido)methane to the formation of a substitution product, bis[(trifluoromethylsulfonyl)aminomethyl]succinamide, or to a cyclization product, N-[trifluoromethylsulfonyl)aminomethyl]succinimide. The attempt to obtain the latter by the reaction of the trifluoromethanesulfonamide sodium salt CF3SO2NHNa with N-chloromethylsuccinimide unexpectedly resulted in N,N-bis(succinimidomethyl)-trifluoromethanesulfonamide. Analogously the reaction of CF3SO2NHNa with N-chloromethyl-phthalimide gave N,N-bis(phthalimidomethyl)trifluoromethanesulfonamide. The reaction of CF3SO2NHNa with succinimide and phthalimide in water and alcohol solution resulted in the ring opening and further transformation of the formed monosubstituted N-(trifluoromethylsulfonyl)amides of succinic and phthalic acids.
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Original Russian Text © M.Yu. Moskalik, V.I. Meshcheryakov, B.A. Shainyan, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 11, pp. 1654–1659.
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Moskalik, M.Y., Meshcheryakov, V.I. & Shainyan, B.A. Reaction of γ-dicarboxylic acids amides and imides with trifluoromethanesulfonamide and formaldehyde. Russ J Org Chem 45, 1644–1650 (2009). https://doi.org/10.1134/S1070428009110116
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DOI: https://doi.org/10.1134/S1070428009110116