[C:1]([CH2:3][C:4]([NH:6][C:7]1[N:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([CH3:12])=[N:10][CH:11]=1)=[O:5])#[N:2].C([O-])(=O)C.[Na+].[Cl:24][C:25]([Cl:29])([Cl:28])[C:26]#[N:27]>C(O)C>[NH2:27][C:26]([C:25]([Cl:29])([Cl:28])[Cl:24])=[C:3]([C:1]#[N:2])[C:4]([NH:6][C:7]1[N:8]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:9]([CH3:12])=[N:10][CH:11]=1)=[O:5]To a solution of 2-cyano-N-(2-methyl-3-phenyl-imidazol-4-yl)acetamide (100 mg, 0.4162 mmol) in Ethanol (1.5 mL) was sequentially added sodium acetate (68.28 mg, 0.8324 mmol), 2,2,2-trichloroacetonitrile (0.051 mL, 0.5016 mmol) and the reaction was stirred at room temperature for 4 h. A further 10 mg of sodium acetate and 10 uL 2,2,2-trichloroacetonitrile was sequentially added and the mixture was stirred for a further 2 h at RT. The reaction was concentrated in vacuo and the residue was partitioned between water and EtOAc. Combined organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo to give 3-amino-4,4,4-trichloro-2-cyano-N-(2-methyl-1-phenyl-1H-imidazol-5-yl)but-2-enamide as a redish oil. (153 mg, 79%). MS (ES+) 384.0.
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