N-(Phenylmethyl)thiourea → HCID 10274859, compound

Participants

Reaction Steps

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (Example 26, Step 2) (0.415 g, 1.12 mmol) in isopropanol (12 mL) in a 25 mL round bottom flask was added N-benzyl thiourea (0.186 g, 1.12 mmol). The solution was heated to reflux (30 hours), cooled to room temperature and let stand for 7 days. The resulting suspension was concentrated in vacuo. The resulting residue was suspended in methylene chloride (100 mL) and washed with NaHCO3 saturated solution (3×10 mL), dried over sodium sulfate, filtered and reconcentrated in vacuo yielding 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-benzylaminothiazole as a pale yellow solid (0.34 g, 69%): mp 112° C. 1H NMR (CDCl3 400 mHz δ7.74 (d, J=8.56 Hz, 2H), 7.43-7.25 (m, 10H), 6.92 (t, J=8.56 Hz, 2H), 4.33 (s, 2H), 3.02 (s, 3H). MS (EI-thermospray): m/z 439 (MH+). HRMS Δ=1.6 mmu.

Provenance & Evidence