[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)[O:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.ClCCl.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.N1C=CC=CC=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:15][CH:14]=3)[O:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1under an N2 atmosphere, 4-(4-(3-chlorophenyl)oxazol-2-yl)benzenamine (0.127 g, 0.469 mmol) was dissolved in dichloromethane (4.00 ml, 62.2 mmol). Benzoyl chloride (0.0572 ml, 0.493 mmol) was added followed by pyridine (0.200 ml, 2.47 mmol), and the reaction was allowed to stir at room temperature for 2.5 hours. The reaction was diluted with ethyl acetate and washed with 0.1N N HCl, and 5% NaHCO3. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude solid was triturated with ethyl acetate/hexanes and the resulting solid was collected by filtration to afford N-(4-(4-(3-chlorophenyl)oxazol-2-yl)phenyl)benzamide (0.112 g, 63.7% yield). ESI m/z=375.1 (M+H+).
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