[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([I:13])=[N:10][C:9]=1[C:14]([OH:16])=O.C1C=CC2N(O)N=[N:23]C=2C=1.CCN=C=NCCCN(C)C.[NH4+].[OH-]>C(Cl)Cl.CN(C=O)C.O1CCOCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([I:13])=[N:10][C:9]=1[C:14]([NH2:23])=[O:16]To a solution of 5-(2-chlorophenyl)-2-iodo-1,3-oxazole-4-carboxylic acid (20.0 g, 57.3 mmol) in DCM (400 mL) and DMF (200 mL) were added HOBt (8.0 g, 60.0 mmol) and EDCI (15.0 g, 80.0 mmol). The reaction mixture was allowed to stir at rt for 2 h and then NH4OH (20 mL) in 1,4-dioxane (400 mL) was added. The reaction mixture was allowed to stir at rt overnight and then was diluted with EtOAc and washed with brine. The organic solution was dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give 5-(2-chlorophenyl)-2-iodo-1,3-oxazole-4-carboxamide (18.0 g, 85%).
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