CS[C:3]1[S:4][C:5]2[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1.[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([CH2:23][C:24]#[N:25])[N:18]=1.C(=O)([O-])[O-].[K+].[K+].CC(=O)OCC>C(O)C>[N+:12]([C:10]1[CH:9]=[CH:8][C:6]2[NH:7][C:3](=[C:23]([C:19]3[N:18]=[C:17]([C:16]([F:27])([F:15])[F:26])[CH:22]=[CH:21][N:20]=3)[C:24]#[N:25])[S:4][C:5]=2[CH:11]=1)([O-:14])=[O:13]To a solution of 2-(methylthio)-6-nitro-1,3-benzothiazole (226 mg, 1.0 mmol) in ethanol (3.5 mL) was added 2-(4-trifluoromethylpyrimidin-2-yl)acetonitrile (187 mg, 1.0 mmol) and potassium carbonate (207 mg, 1.5 mmol). The orange mixture was heated in the microwave at 160° C. for 15 min, then cooled and poured into EA (60 mL). The organic layer was washed twice with 1N hydrochloric acid (25 mL each), brine (25 mL), and water (5 mL), then dried with magnesium sulfate, filtered, and concentrated under reduced pressure to give 2-(6-nitrobenzothiazol-2(3H)-ylidene)-2-(4-trifluoromethylpyrimidin-2-yl)acetonitrile (349 mg, 96% yield) as a yellow solid.
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