[In].[Cl-].[NH4+].[Cl:4][C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1>C(O)C.Cl>[Cl:4][C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1Indium powder (0.64 mg, 2.5 mmol) and saturated ammonium chloride solution (3 ml, 2.5 mmol) are added to a solution of 2-chloro-4-methyl-5-(4-nitro-phenyl)-thiazole (25b) (0.20 g, 0.786 mmol) in ethanol (3 ml). The mixture is heated at reflux with stirring for 90 minutes. When cool the mixture is diluted with 2M aqueous hydrochloric acid to dissolve any product and the mixture is filtered through celite. The filtrate is adjusted to pH 9 with aqueous sodium hydroxide and extracted with dichloromethane (3×30 ml). The combined organic extract is dried (MgSO4) filtered, and the solvent removed to give the title compound as a yellow solid (0.17 g).
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