Lithium iodide → HCID 10088818, compound

Participants

Reaction Steps

A solution of 3-[2-(4-isopropyl-3-methyl-phenoxy)thioacetylamino]benzoate (0.50 g, 1.4 mmol) in pyridine (15 mL) was treated with anhydrous lithium iodide (1.87 g), and the resulting mixture was heated to reflux for 10 h. The solution was cooled and evaporated, and the residue was partitioned between 1 N aqueous HCl and ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered and evaporated. The residual solid was purified by column chromatography to afford the title product (0.22 g, 0.64 mmol, 46%). m.p. 174–176° C. 1H NMR (CDCl3, 300 MHz): δ 9.84 (1H, br s), 8.39 (1H, t, J=2 Hz), 8.28 (1H, ddd, J=8, 2, 1 Hz), 8.00 (1H, dt, J=8, 2 Hz), 7.55 (1H, t, J=8 Hz), 7.19 (1H, d, J=8 Hz), 6.83–6.77 (2H, m), 4.97 (2H, s), 3.03 (1H, m, J=7 Hz), 2.32 (3H, s), 1.20 (6H, d, J=7 Hz). Mass spectrum (ES−): m/z 342. Elemental analysis: calculated for C19H21NO3S C, 66.45; H, 6.16; N, 4.08. observed C, 66.71; H, 6.65; N, 4.02.

Provenance & Evidence