Chemical Properties
WHITE CRYSTALS OR CRYSTALLINE POWDER
Uses
N-Methyltrifluoroacetamide is a useful synthetic intermediate. It is used to prepare electrophilic 11b-aryl derivs. of estradiol as steroidal affinity labels of the estrogen receptor a. It is also used to synthesize amino substituted derivatives of 5'-amino-5'-deoxy-5'-noraristeromycin as antiviral agent.
General Description
The high-resolution proton and fluorine resonance spectra of
N-methyltrifluoroacetamide in tetrahydrofuran and acetone was studied.
Synthesis
Example 6-B: Trifluoroacetamide (300 mg; 0.63 mmol) was dissolved in THF (2 mL) at 0 °C, NaH (60% mineral oil dispersion, 50 mg; 0.63 mmol) was added, followed by dropwise addition of MeI (60 μL; 0.94 mmol). The reaction mixture was stirred overnight at room temperature. After completion of the reaction, THF was removed by evaporation and the residue was diluted with water and extracted with CH2Cl2. The organic layers were combined, washed with saturated brine and dried over anhydrous Na2SO4. After concentration, the crude product was purified by rapid chromatography on silica gel (eluent: hexane/ethyl acetate, gradient from 4:1 to 1:1) to afford N-methyl-2,2,2-trifluoroacetamide 200 mg in 65% yield.
References
[1] Patent: US2003/105094, 2003, A1
