4-Methoxybenzenecarbothioamide → HCID 22911832, compound

Participants

Reaction Steps

To a solution of 2-bromo-1- (4-fluorophenyl) -2- (4-methylsulfonylphenyl) ethanone (Example 26, Step 2) (0.500 g, 1.35 mmol) in isopropanol (10 mL) in a 25 mL round bottom flask was added p-methoxythiobenzamide (0.230 g, 1.35 mmol). The solution was heated to reflux for 30 hours and cooled to room temperature. The resulting suspension was concentrated in vacuo, suspended in methylene chloride (100 mL) and washed with NaHCO3 saturated solution (3×10 mL), dried over sodium sulfate, filtered and concentrated yielding 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(4-methoxyphenyl)thiazole (0.360 g, 61%) as a crystalline solid: mp 187°-189° C., 1HNMR (CDCl3) 300 mHz 7.99 (d, 8.82 Hz, 2 H), 7.93 (d, J=8.50 Hz, 2 H), 7.63-7.53 (m, 4 H), 7.09 (t, J=8.63 Hz, 2 H), 7.03 (d, J=8.82 Hz, 2 H), 3.92 (s, 3 H), 3.13 (s, 3 H); MS m/z 440 (M+H). HRMS Δ=2.0 mmu.

Provenance & Evidence