2,2-Dimethylpropanethioamide → 2-(Tert-butyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole

Participants

Reaction Steps

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylthiophenyl)ethanone (Example 1, Step 3) (0.196 g, 0.578 mmol) in ethanol (6 mL) in a 25 mL round bottom flask was added 2,2-dimethylthiopropionamide from Step 1 (0.071 g, 0.606 mmol) and the mixture heated to reflux overnight. The reaction was cooled to room temperature, diluted with ethyl acetate (50 mL) and this solution washed successively with Na2CO3 (10% solution) and brine, dried over Na2SO4, filtered and concentrated in vacuo yielding 2-(tert-butyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole as a pale yellow oil (0.162 g, 78%): 1H NMR (CDCl3) 300 mHz δ7.56-7.51 (m, 2H), 7.24 (d, J=8.48 Hz, 2H), 7.20 (d, J=8.48 Hz, 2H), 6.98 (t, J=8.85 Hz, 2H), 2.49 (s, 3H), 1.52 (s, 9H). MS (EI): m/e 357 (M+). HRMS Δ=0.1 mmu.

Provenance & Evidence