Cl.[NH2:2][CH2:3][C:4](=O)[C:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)([CH3:7])[CH3:6].[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[S:28])=[CH:22][CH:21]=1.CCN(CC)CC>C1C=CC=CC=1>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([C:5]([C:4]2[N:26]([C:23]3[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=3)[C:27](=[S:28])[NH:2][CH:3]=2)([CH3:7])[CH3:6])[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]A mixture of 1-amino-3-(3,4-dimethoxyphenyl)-3-methylbutan-2-one hydrochloride (210 mg, 0.77 mmol), 4-fluorophenyl isothiocyanate (141 mg, 0.92 mmol), and Et3N (0.16 mL, 1.15 mmol) in benzene (7 mL, anhyd) was refluxed for 8 h. The volatiles were removed under reduced pressure. The residue was combined with acetic acid (5 mL) and heated at reflux 4 h. After concentration, the crude product was purified by flash chromatography to provide 5-(2-(3,4-dimethoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2(3H)-thione (260 mg, 91%). 1H NMR (400 MHz, CDCl3) δ 10.35 (s, 1H), 6.87 (t, 2H), 6.80 (d, 1H), 6.67 (d, 1H), 6.62-6.59 (m, 2H), 6.48 (d, 1H), 6.46 (s, 1H), 3.87 (s, 3H), 3.75 (s, 3H), 1.44 (s, 6H).
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