[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.
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
Michael L. Edwards
Marion Merrell Dow, Cincinnati, OH, USA