Ethanol → 4-(4-Methylphenyl)thiazole

Participants

Reaction Steps

A 100 mL one-neck round-bottom flask, equipped with provisions for magnetic stirring, was charged with 2-(2-chlorophenyl)-4-(4-methylphenyl)-5-(4-methylthiophenyl)thiazole from Step 4 (0.243 g, 0.596 mmol) and aqueous ethanol (25 mL). Oxone®(1.10 g, 1.787 mmol) was added, and the suspension was stirred at room temperature for 16 hours. Water (25 mL) was added, and the product precipitated. The suspension was cooled to 0° C. and held for one hour. The product was filtered, washed with water (25 mL), and dried to yield 2-(2-chlorophenyl)-5-methylsulfonylphenyl)-4-(4-methylphenyl)thiazole (0.236 g, 90%) as a white solid: mp 185°-187 ° C. 1H NMR (CDCl3) 300 MHz 8.40(m, 1H), 7.89(d, J=8.26 Hz, 2H), 7.61 (d, J=8.46 Hz, 2H), 7.54-7.37 (m, 5H), 7.16 (d, J=7.85 Hz, 2H), 3.09(s, 3H), 2.38(s, 3H). Mass spectrum: MH+ =439.

Provenance & Evidence