Hydrochloric Acid → HCID 10115851, compound

Participants

Reaction Steps

A solution of 2-(4-iodo-2-methyl-phenylamino)-3,4,5-trifluoro-N-(2-vinyloxyethoxy)-benzamide (3.00 g, 6.09 mmol) in ethanol (80 mL) was treated with 1 M aqueous hydrochloric acid (16 mL, 16 mol). The resultant solution was stirred for 2.5 h at ambient temperature. Water (50 mL) was added and the slurry was filtered. The solids were washed with ethanol-water (1:1, 150 mL) and recrystallized from methanol-acetone to afford N-(2-hydroxyethoxy)-2-(4-iodo-2-methyl-phenylamino)-3,4,5-trifluoro-benzamide (2.12 g, 75%): m.p. 205-207° C. (dec); 1H NMR (400 MHz, DMSO-d6) δ 11.85 (br s, 1 H), 8.13 (s, 1 H), 7.54 (dd, J=8.9, 8.7 Hz, 1 H), 7.47 (d, J=1.0 Hz, 1 H), 7.32 9d, J=8.5 Hz, 1 H), 6.41 (dd, J=8.1, 5.0 Hz, 1 H), 4.69 (br s, 1 H), 3.79 (br s, 2 H), 3.52 (br s, 2 H), 2.20 (s, 3 H); MS (APCI+)=467.1; MS (APCI−)=465.1; Anal. Calcd/found for C16H14F3IN2O3: C, 41.22/41.28; H, 3.03/2.91; N, 6.01/5.79.

Provenance & Evidence