[CH2:1]([O:6][C:7]1[CH:25]=[CH:24][C:10]([C:11]([NH:13][CH2:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)=O)=O)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27].C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:1]([O:6][C:7]1[CH:25]=[CH:24][C:10]([C:11]2[S:27][C:15]([C:17]3[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=3)=[CH:14][N:13]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5]To a solution of 2-(4-pentyloxybenzamido)-4′-bromoacetophenone (3.39 g) in tetrahydrofuran (34 ml) was added phosphorus pentasulfide (2.43 g), and refluxed for 30 minutes. The reaction mixture was cooled, and poured into saturated sodium hydrogen carbonate aqueous solution (400 ml), and stirred for 1.5 hours. The resulting precipitate was collected by filtration to give 2-(4-pentyloxyphenyl)-5-(4-bromophenyl)thiazole (2.32 g).
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