3-Phenylpropanethioamide → 4-(4-Fluorophenyl)-5-(4-methylthiophenyl)-2-(2-phenylethyl)thiazole

Participants

Reaction Steps

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylthiophenyl)ethanone (Example 1, Step 3)(0.115 g, 0.340 mmol) in ethanol (4 mL) in a 10 mL round bottom flask was added 3-phenylthiopropionamide from Step 1 (0.059 g, 0.357 mmol) and the mixture was heated to reflux overnight. The reaction was cooled to room temperature, diluted with ethyl acetate (50 mL), washed with Na2CO3 (10% solution), brine, dried over Na2SO4, filtered and concentrated in vacuo yielding 4-(4-fluorophenyl)-5-(4-methylthiophenyl)-2-(2-phenylethyl)thiazole (0.090 g, 65%) as oily crystals: mp 97°-99° C.; 1HNMR (CDCl3) 300 mHz 7.50 (d of d, J=5.38 and 8.80, 2 H), 7.35-7.15 (m, 9H), 6.99 (t, J=8.80, 2H), 3.35 (t, J=8.80, 2 H), 3.19 (t, J=8.56 Hz, 2H), 2.49 (s, 3H); MS (EI) m/z 405.10 (MH+), HRMS (M+) Δ=0.0 mmu.

Provenance & Evidence