4-Phenylbutanethioamide → HCID 54368480, compound

Participants

Reaction Steps

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylthiophenyl)ethanone (Example 1, step 3) (0.100 g, 0.295 mmol) in ethanol (3 mL) in a 10 mL round bottom flask was added 4-phenylthiobutyramide from step 1 (0.055 g, 0.310 mmol) and the mixture 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. The crude thiazole was flash chromatographed (9:1, hexane:ethyl acetate) yielding 4-(4-fluorophenyl)-5-(4-methylthiophenyl)-2-(3-phenylpropyl)thiazole (0.118 g, 95%) as crystalline solid: mp 62°-63° C.; 1HNMR (CDCl3) 300 mHz 7.49 (d of d, J=5.52 and 8.85, 2H), 7.33-7.14 (m, 9H), 6.98 (t, J=8.85, 2H), 3.05 (t, J=7.74, 2 H), 2.82 (t, J=7.74 Hz, 2H), 2.49 (s, 3H), 2.18 (m, 2 H); MS (FAB) m/z 420 (MH+).

Provenance & Evidence