Potassium Iodide → N-[4-chloro-3-(trifluoromethyl)phenyl]-2-{(3-(1H-tetrazol-1-yl)-phenyl]oxy}acetamide

Participants

Reaction Conditions

Reaction Steps

To a 50 mL recovery flask was added 2-chloro-N-(4-chloro-3-trifluoromethylphenyl)-acetamide (400 mg, 1.47 mmol, 1.0 eq.) and 1-(3-aminophenyl)-1H-tetrazole 11 (710 mg, 4.40 mmol, 3 eq.) and DMF (10 mL). A catalytic amount of potassium iodide was added. The reaction mixture was heated at 70° C. overnight. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with a succession of 10% aq. LiCl (3×50 mL) and sat'd aq. NaCl (50 mL). The combined aqueous phases were extracted with ethyl acetate (2×50 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated to give a tan solid. The solid was recrystallized in methanol and acetonitrile (10:1) to give a white solid (63 mg). Subsequent crops were isolated from the mother liquor (91 mg). Total yield: 154 mg, 26%. LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 397.1 (M+H)+1 1H-NM, Varian 400 MHz (DMSO-d6) δ 10.51 (s, 1H), 10.00 (s, 1H), 8.19 (d, 1H), 7.88-7.85 (dd, 1H), 7.65 (d, 1H), 7.34-7.30 (t, 1H), 7.09 (t, 1H), 7.05-7.03 (dd, 1H), 6.75 (dd, 1H), 6.74 (t, 1H), 4.00 (d, 2H) ppm.

Provenance & Evidence