Triethylamine → N-methoxy-N-methyl-1-(trifluoromethyl)cyclopropane-1-carboxamide

To a solution of N,O-dimethyl hydroxylamine hydrochloride (0.48 g, 4.87 mmol, Aldrich) in DMF (15 mL, Aldrich) was added triethylamine (0.68 mL, 4.87 mmol, Aldrich). After completed addition the reaction was stirred at RT for 5 min. 1-trifluoromethylcyclopropane-1-carboxylic acid (0.5 g, 3.24 mmol, Alfa Aesar, A Johnson Matthey Company) was added and the reaction was stirred at room temperature for 1 min. The reaction was cooled to 0° C. and propylphosphonic anhydride solution (50 wt. % in DMF; 3.10 mL, 4.87 mmol, Acros Organics) was added dropwise. The resulting mixture was stirred at room temperature for 5 days. The reaction was quenched with saturated NaHCO3 and stirred at RT for 5 min. The reaction was extracted with diethyl ether (2×40 mL) and the combined organic extracts were washed with saturated ammonium chloride, water, dried over MgSO4, and concentrated to give 229 mg of the title compound as a light yellow liquid. MS (ESI, positive ion) m/z: 198.1 (M+H).

1. additionaddition the reaction
2. stirringthe reaction was stirred at room temperature for 1 min
3. temperatureThe reaction was cooled to 0° C.
4. stirringThe resulting mixture was stirred at room temperature for 5 days
5. customThe reaction was quenched with saturated NaHCO3
6. stirringstirred at RT for 5 min
7. extractionThe reaction was extracted with diethyl ether (2×40 mL)
8. washthe combined organic extracts were washed with saturated ammonium chloride, water
9. dry with materialdried over MgSO4
10. concentrationconcentrated

ORD record

ord-5617fb8d18944a948c1503214ae269de

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2