Hydrogen Peroxide → HCID 22615167, compound

Participants

Reaction Steps

A solution of 400 mg (1.13 mmole) of N-(3-fluoropyrid-2-yl)eth-2-yl-N'-(5-bromopyrid-2-yl)-thiourea (see Example 920 of W093/03022) in 11.5 ml of glacial acetic acid was treated with 0.8 ml (7.83 mmole) of 30% hydrogen peroxide. After stirring 1.5 hrs at room temperature, the solution was concentrated and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate (1×). The organic layer was back washed with brine (1×) and dried over sodium sulfate. Purification by flash silica gel chromatography (50% ethyl acetate/hexanes) gave 75 mg (19.6%) of the titled compound as a white solid: mp 151°-154° C.; IR (KBr, cm-1) 3200, 3100, 3000, 1685, 1557, 1467, 1360, 1290, 1230, 839; 1H NMR (300 MHz, DMSO-d6) δ 9.30 (br. s., 1H), 8.40 (d, 1H), 8.22 (d, 1h), 7.85 (dd, 1H), 7.79 (br.t., 1H), 7.70 (dt, 1H), 7.45 (d, 1H), 7.30-7.40 (m, 1H), 3.58 (q, 2H), 3.00 (t, 2); MS (FD) m/e 340 (Mt). Anal. Calc'd. for C13H12BrFN4O: C, 46.04; H, 3.57; N, 16.52. Found: C, 46.25; H, 3.66; N, 16.54.

Provenance & Evidence