Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=2)[N:6]=1.[NH:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[CH:21]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[N:20]1([C:2]2[O:3][C:4]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=3)[N:6]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[CH:21]1A mixture of methyl 3-[2-chloro-4-(3-chlorophenyl)-5-oxazolyl]propionate (2.31 g), 1H-benzoimidazole (1.82 g), potassium carbonate (3.19 g) and N,N-dimethylformamide (12 mL) was stirred at 120° C. for 2 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and methyl 3-[2-(1H-benzoimidazol-1-yl)-4-(3-chlorophenyl)-5-oxazolyl]propionate (1.85 g, 63%) was obtained as a solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).
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