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 (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-9e3a1b7d27404be88a9c756fb341948e

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627456B1