Ethyl trifluoroacetate → 2,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamide

Temperature

0 °C

This compound has been prepared using a literature method (K. A. Cruickshank, D. L. Stockwell (1988) Tetrahedron Lett. 29, 5221). Propargylamine (90.9 mmol, 5 g, 6.227 mL) was added to methanol (90 mL) and the solution cooled to 0° C. Ethyl trifluoroacetate (1.3 equiv., 118.2 mmol, 16.8 g, 14.1 mL) was added and the mixture stirred at room temperature for 24 h. The solvent was evaporated, the residue diluted with 90 mL chloroform and washed with aqueous NaHCO3 solution (2×75 mL) and water (1×75 mL). The organic layer was evaporated and the orange residue distilled in vacuum to give N-propargyltrifluoroacetamide (13.171 g, 96%) as a colorless liquid which solidifies at -20° C. bp: 41° C./1.5 mm (bp ref.: 51° C./2.5 mm), mp: 31-33° C. 1H-NMR (CDCl3): 2.34 (m, 1H, CH), 4.15 (dd, 2H, CH2), 7.80 (br s, H, NH). 1H-NMR ref. (CDCl3): 2.34 (t, 1H), 4.16 (dd, 2H), 7.00 (br s, 1H). 13C-NMR (CDCl3): 29.4 (CH2), 72.4 (CH), 77.0 (C), 109.859, 113.673, 117.470, 121.276 (CF3, J=286.37 Hz), 156.748, 157.249, 157.750, 158.250 (CO, J=37.77 Hz).

1. customThis compound has been prepared
2. customThe solvent was evaporated
3. additionthe residue diluted with 90 mL chloroform
4. washwashed with aqueous NaHCO3 solution (2×75 mL) and water (1×75 mL)
5. customThe organic layer was evaporated
6. distillationthe orange residue distilled in vacuum

ORD record

ord-e4832067532943f0951330ff9b079930

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05965364