354-38-1

white to pale yellow or beige crystalline powder

pharmaceutical intermediate

Trifluoroacetamide was used as probe for determination of membrane potential and extra/intracellular volume of erythrocytes by fluorine-19 NMR studies.

One-pot synthetic approach to produce trifluoroacetamide has been developed using an electrochemical method with the B12 complex as a catalyst under mild conditions, in open air at room temperature. Thirty examples of trifluoroacetamide were synthesized from 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) in moderate to good yields. This user-friendly strategy is compatible with a broad range of trifluoroacetamide syntheses.
10.1142/S1088424621500292

Example 5: Synthesis of the blocking isomer trifluoroacetamide 3a The block trans isomer 2a (0.93 g, 1.84 mmol, 503.4 g/mol) as a sulfate was dissolved in 15 mL of ethanol. Under argon protection, triethylamine (1.8 mL, 13 mmol) and ethyl trifluoroacetate (2.2 mL, 18 mmol) were slowly added (Figure 2a). The reaction mixture was stirred for 2.5 h at room temperature. Upon completion of the reaction, the volatiles were removed by distillation under reduced pressure. The resulting residue was dissolved in 300 mL of ethyl acetate and washed sequentially with 2 x 50 mL of 5% hydrochloric acid solution. The organic phase was dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford block-transfer isomerized trifluoroacetamide 3a as an orange solid (0.92 g, 100% yield, 501.4 g/mol). 1H NMR (methanol-d4) δ 8.35 (1H, d); 8.15 (1H, d); 7.80 (1H, s); 6.82 (1H, s); 6.65 (4H, m); 4.82 (2H, s).

[1] Patent: US6448407, 2002, B1
[2] Journal of the American Chemical Society, 1943, vol. 65, p. 1459
[3] Journal of the American Chemical Society, 1943, vol. 65, p. 1459
[4] Journal of Organic Chemistry, 1959, vol. 24, p. 1256,1258
[5] Bulletin de la Classe des Sciences, Academie Royale de Belgique, 1922, vol. <5>8, p. 346