Triethylamine → HCID 59441650, compound

Participants

Reaction Steps

To a solution of 2-trifluoromethoxy-4-amino nitro benzene (5.00 g, 22.5 mmol) in dichloromethane (200 mL) was added triethylamine (12.2 mL, 90 mmol, 4.0 equiv.), dimethylaminopyridine (ca 500 mg) and dimethylaminoacetyl chloride hydrochloride (5.3 g, 33.8 mmol, 1.50 equiv.). The resulting clear solution was stirred 24 hours and was poured into saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, taken to a residue under reduced pressure, and purified by chromatography on SiO2 (0 to 10% methonal/CH2CL2) to give N1-[3-amino-4-(trifluoromethoxy)phenyl]-N2,N2-dimethylglycinamide (4.54 g, 14.8 mmol, 66% yield) as a brown oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.26 (s, 6 H), 3.11 (s, 2 H), 7.67 (dd, J=8.97, 1.28 Hz, 1 H), 8.08 (dd, J=9.06, 2.65 Hz, 1 H), 8.60 (d, J=2.74 Hz, 1 H), 10.40 (s, 1 H).

Provenance & Evidence