Thioacetamide → 4-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-methylthiazole

Participants

Reaction Steps

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (0.437 g, 1.18 mmol) (Example 26, Step 2) in acetonitrile (10 mL) in a 25 mL round bottom flask was added thioacetamide (0.088 g, 1.18 mmol) and the solution heated to reflux (2 hours) until all solid dissolved. The reaction was cooled to room temperature. The acetonitrile was removed in vacuo and the resulting product precipitated from methanol by the addition of water yielding 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-methylthiazole (0.226 g, 55%, ca. 85% purity by 1H NMR): mp 229°-233° C. 1HNMR (CDCl3) 300 mHz δ7.98 (d, J=8.11 Hz, 2H ), 7.66-7.61 (m, 2H), 7.52 (d, J=8.48 Hz, 2H), 7.13 (t, J=8.48 Hz, 2H), 3.31 (s, 1H), 3.10 (s, 3H). MS (EI-thermospray): m/z 348 (M+). HRMS Δ=-2.3 mmu.

Provenance & Evidence