Hydrochloric Acid → HCID 21707726, compound

Participants

Reaction Steps

A solution of anhydrous lithium iodide (2.68 g, 20 mmol, Aldrich) in 25 mL dry pyridine was brought to reflux under a nitrogen atmosphere and treated with 3 (1.95 g, 5 mmol). The reaction was refluxed for 6 h, then allowed to cool to room temperature under a stream of nitrogen. The solution was poured into 1N HCl (300 mL), and extracted with ethyl acetate (3 X 50 mL). The combined ethyl acetate layers were extracted with 5% sodium bicarbonate (4 X 50 mL). The aqueous phase was acidified to pH 2, and extracted with ethyl acetate (3 X 50 mL). The organic phase was dried with Mg2SO4, filtered through activated charcoal, evaporated, and triturated with hexanes to yield a white solid. Yield: 1.71 g (91%). mp 99°-101° C. IR: 3448 (br), 1735, 1595, 1462, 1232, 719 cm-1. 1H NMR (CDCl3, TMS) d 7.656 (dd, J=8.00, 1.71 Hz, 2 H), 7.299-7.254 (m, 3 H), 7.036 (t, J=7.98 Hz, 1 H), 6.794-6.773 (m, 1 H), 6.573 (d, J=7.55 Hz, 1 H), 6.251 (s, 1 H), 4.955 (s, 1 H), 4.357 (s, 2 H), 2.728-2.620 (m, 4 H), 1.914-1.868 (m, 2 H). 13C NMR (CDCl3, TMS) d 173.47, 156.32, 139.01, 137.40, 130.50, 128.12, 128.07, 127.56, 122.02, 115.43, 113.66, 80.56, 66.13, 64.73, 27.26, 26.96, 24.67. Anal. Calcd. for C19H20O4S2 : C, 60.62; H, 5.35. Found: C, 60.36; H, 5.21.

Provenance & Evidence