Dichloromethane → HCID 54412494, compound

Participants

Reaction Steps

To a solution of 2-bromo-2-(4-fluorophenyl)-1-(4-methylthiophenyl) ethanone from Step 2 (0.70 g, 2.10 mmol) in ethanol (20 mL) in a 50 mL round bottom flask was added thioacetamide (0.16 g, 2.10 mmol) and the mixture heated to reflux for 20 hours. The reaction was cooled to room temperature and concentrated in vacuo and dissolved in methylene chloride. This solution was washed with NaHCO3 saturated solution and dried over Na2SO4, filtered and reconcentrated in vacuo yielding a white crystalline solid. Flash chromatography of this solid (2:1 methylene chloride: hexane) yielded 5-(4-fluorophenyl)-4-(4-methylthiophenyl) -2-methylthiazole as a white solid (0.45 g, 68%): mp 104°-105° C. 1H NMR (CDCl3) 400 mHz δ7.39 (d, J=8.32, 2H), 7.28 (dd, J=8.80, 5.14, 2H), 7.15 (d, J=8.32, 2H), 7.00 (t, J=8.80, 2H), 2.74 (s, 3H), 2.47 (s, 3H). MS (EI): m/z 316 (M+H). HRMS Δ=0.000 mmu.

Provenance & Evidence