p-Toluenesulfonic acid → HCID 12150685, compound

Participants

Reaction Steps

A mixture of p-toluenesulfonic acid (169 mg, 0.98 mmol) and 2-{[3,5-Dichloro-4-(3-ethanesulfonyl-4-hydroxy-phenoxy)-phenyl]-hydrazono}-propionic acid ethyl ester (310 mg, 0.65 mmol) in toluene (2.5 mL) was heated to reflux for 16 hours and then cooled to room temperature. The reaction mixture was diluted with ethyl acetate (25 mL), washed with saturated NaHCO3 (3 times 10 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative thin layer chromatography (4% methanol in methylene chloride) to afford the title compound (100 mg) as a tan solid. 1H NMR (400 MHz, CDCl3) δ10.7 (s, 1H), 7.42 (s, 1H), 7.18 (d, 1H), 7.04-6.98 (m, 2H), 6.88 (d, 1H), 4.36-4.30 (q, 2H), 3.20-3.05 (q, 2H), 1.34 (t, 3H), 1.18 (t, 3H). MS (APCI−) Calc: 457.0, Found: 456.1 (M−1).

Provenance & Evidence