Methylthiourea → HCID 22911797, compound

Participants

Reaction Steps

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (Example 26, Step 2) (0.355 g, 0.959 mmol) in ethanol (10 mL) in a 25 mL round bottom flask was added N-methylthiourea (0.086 g, 0.959 mmol). The solution was heated to reflux for 14 hours and cooled to room temperature. The resulting suspension was concentrated in vacuo, suspended in ethyl acetate (100 mL) and washed with NaHCO3 saturated solution (3×10 mL), dried over sodium sulfate and filtered. Isooctane was added to the filtrate until the solution became cloudy yielding a pale yellow fluffy solid which was collected by vacuum filtration. This solid was dissolved in methylene chloride and washed with sodium carbonate solution (10% solution), dried over sodium sulfate, and concentrated yielding a solid. This solid was recrystallized from methylene chloride-isooctane yielding 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-methylaminothiazole (0.135 g, 39%) as a pale yellow powder: mp 243°-244° C.; 1HNMR 400 mHz 7.90 (q, J=4.76 Hz, 1 H), 7.81 (d, J=8.50 Hz, 2 H), 7.49-7.43 (m, 2 H), 7.41 (t, J=8.70 Hz, 2 H), 7.19 (t, J=8.95 Hz, 2 H), 3.22 (s, 3 H), 2.90 (d, J=4.80 Hz, 3 H); MS (FAB) m/z 363 (M+H). HRMS Δ=-0.2 mmu.

Provenance & Evidence