N-MethyltrifluoroMethanesulfonaMide is a dioxane that is used as an intermediate for the production of other chemicals. It has been shown to form bifurcated intramolecular hydrogen bonds and isomers with stereospecificity. The molecule can be prepared by reacting methylamine with chlorotrifluoromethane followed by hydrolysis of the resulting N-MethyltrifluoroMethanesulfonaMide chloride. This compound is soluble in both water and organic solvents, such as methanol, ethanol, acetone, and chloroform. It has been found to have a high affinity for amines and amides and will form hydrogen bonds with these compounds.
N,N-Diethyl-1,1,1-trifluoromethanesulfonamide is used in the preparation of hexaalkylguanidinium trifluoromethanesulfonates from tetraalkylureas, triflic anhydride and secondary amines and their properties as ionic liquids.
N-MethyltrifluoroMethanesulfonaMide is 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.
