C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[Cl:13][C:14]1[CH:15]=[C:16]([N:21]2[CH:25]=[C:24]([C:26]([OH:28])=O)[N:23]=[CH:22]2)[CH:17]=[CH:18][C:19]=1[Cl:20].N.O>CN(C=O)C>[Cl:13][C:14]1[CH:15]=[C:16]([N:21]2[CH:25]=[C:24]([C:26]([NH2:3])=[O:28])[N:23]=[CH:22]2)[CH:17]=[CH:18][C:19]=1[Cl:20]Carbonyldiimidazole (0.49 g, 3 mmol) was added to a stirred suspension of 1-(3,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid (0.64 g, 2.5 mmol) in DMF (10 ml). After 1 h at 60° C., the reaction mixture was cooled to rt, aqueous ammonia (25%, 20 ml) was added and stirring was continued for 12 h. Then H2O (100 ml) was added and the precipitated product was filtered. Recrystallisation from EtOH afforded the title compound as off-white crystals. Mp. 244-245° C. (EtOH), MS: m/e=255 (M+).
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