[C:1]1([CH2:7][CH2:8][NH:9][C:10]([NH2:12])=[S:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)=O.CN(C)C=O>O>[C:1]1([CH2:7][CH2:8][NH:9][C:10]2[S:11][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][CH:18]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1A mixture of N-(2-phenylethyl)thiourea (3.60 g, 20 mmol), 2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone (5.34 g, 20 mmol) and N,N-dimethylformamide (5 mL) was stirred at room temperature for 16 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained solid was washed with hexane to give the title compound (5.2 g, yield 74%) as pale-yellow crystals.
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