[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=O.C(=O)(O)[O-].[Na+]>CCO>[CH3:7][C:5]1[N:6]2[CH:9]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=3)[N:1]=[C:2]2[S:3][CH:4]=1A mixture of 2-amino-4-methylthiazole (0.24 g, 2.11 mmol) and 2-bromo-4′-nitroaceto phenone (0.5 g, 2.05 mmol) in EtOH (20 ml) was heated under reflux for 16 h. The reaction mixture was allowed to cool and sodium bicarbonate (200 mg, 2.38 mmol) was added and heating was continued for 1 h. On cooling to room temperature, the solvent was removed under reduced pressure and DCM (75 ml) was added to the residue. The insoluble material was collected by filtration and purified by flash chromatography (50:1 DCM/MeOH) to give the title compound (0.266 g, 50%) as a yellow solid.
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