[H-].[Na+].[SH:3][C:4]1[N:5]([CH3:9])[CH:6]=[CH:7][N:8]=1.[H][H].F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].[Cl-].[Na+]>CN(C)C=O>[CH3:9][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[S:3][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]To a slurry of 0.8 g (20 mmoles) of sodium hydride (60% dispersion in mineral oil) in 10 ml of N,N-dimethylformamide, stirred in an ice bath, and under a nitrogen atmosphere, was added dropwise a solution of 2.28 g (20 mmoles) of 2-mercapto-1-methylimidazole in 5 ml of N,N-dimethylformamide. After the evolution of hydrogen gas had ceased, the ice bath was removed and the reaction mixture stirred at room temperature for 0.5 hours. To the reaction was added, dropwise, a solution of 2.82 g (20 mmoles) of 1-fluoro-2-nitrobenzene in 10 ml of N,N-dimethylformamide. After stirring at room temperature for 16 hours, the mixture was poured into a saturated sodium chloride solution (100 ml) and extracted with dichloromethane. The organics were dried and the solvents were removed in vacuo. The resulting yellow solid was triturated with ether and collected by filtration to give 3.5 g (74%) of product as yellow prisms, mp 117°-119° C.
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