Ammonium Chloride → HCID 44185965, compound

Participants

Reaction Steps

A suspension of iron powder (4 equivalents, 78 mg, 1.4 mmol) and ammonium chloride (5.8 equivalents, 109 mg, 2 mmol) in ethanol (400 μL) and water (438 μL) was heated to reflux. 1-(4-(2-amino-3-nitropyridin-4-yl-oxy)-2-(methylthio)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea (180 mg, 0.35 mmol) was added in portions and the mixture stirred at reflux for 24 hours. After cooling to room temperature, the slurry mixture was filtered and washed with ethanol. After removal of the solvent, the crude powder was dissolved into EtOAc, filtered to removed the precipitate, and evaporated to provide the title compound (100 mg, 59%) as a sticky dark oil. 1H-NMR (δ, ppm, DMSO-d6): 2.41 (s, 3H, CH3), 5.61 (s, 2H, NH2,Py), 6.06 (d, 1H, HPy,5, J=5.6 Hz), 6.79 (d, 1H, Harom, J=8.7 Hz), 7.01 (s, 1H, Harom), 7.26 (d, 1H, HPy,6, J=5.6 Hz), 7.58-7.69 (m, 4H, Harom), 8.12 (s, 2H, NH2,Py), 8.27 (s, 1H, NHurea1), 10.02 (s, 1H, NHurea3). LC-MS (m/z): 484 (M+H, 100).

Provenance & Evidence