N-Methyltrifluoromethanesulfonamide

[34310-29-7]  · C2H4F3NO2S  · N-Methyltrifluoromethanesulfonamide  · (MW 163.14)

(methylamine derivative found to react with alcohols under Mitsunobu conditions to give derivatized secondary amines)

Physical Data: bp 90-94 °C/20 mmHg.1

Solubility: sol THF, chloroform, methylene chloride.

Form Supplied in: clear liquid.

Preparative Method: prepared from methylamine and Trifluoromethanesulfonic Anhydride as follows. Methylamine (25.5 g, 0.5 mol) is added to chilled (-70 °C) dichloromethane (250 mL). A solution of triflic anhydride (28.2 g, 0.1 mol) in dichloromethane (20 mL) is added dropwise and the mixture is stirred at -70 °C for 3 h. The mixture is washed with 1N HCl (2 × 250 mL) and the organic layer is separated and dried (MgSO4). The solvent is removed at atmospheric pressure by slow distillation through a column (500 cm × 20 cm) packed with glass helices (product codistills with solvent and evaporation on a rotary evaporator gives very low yields). The residue is distilled to give 9.3 g (57%) of a clear liquid, bp 95-98 °C/30 mmHg.

Secondary Amines.

Alcohols react with this compound in THF under Mitsunobu conditions to give derivatized secondary amines.2 The reaction proceeds with inversion of configuration (eq 1).2


1. Trepka, R. D.; Harrington, J. K.; Beliale, J. W. JOC 1974, 39, 1094.
2. Edwards, M. L.; Stemerick, D. M.; McCarthy, J. R. TL 1990, 31, 3417.

Michael L. Edwards

Marion Merrell Dow, Cincinnati, OH, USA



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