[H-].[Na+].[CH3:3][O:4][NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7].F[C:17]1[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][C:18]=1[N+:25]([O-:27])=[O:26].ClC1C=CC(SC)=CC=1[N+]([O-])=O>CN(C=O)C.O>[CH3:3][O:4][N:5]([S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[C:17]1[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][C:18]=1[N+:25]([O-:27])=[O:26]To a suspension of sodium hydride (60%, 0.33 g (8.17 mmol)) in DMF (10.0 ml), N-methoxy-p-toluenesulfonamide (1.63 g (8.17 mmol)) was added with stirring under cooling with ice. To the resulting mixture, after 15 minutes' stirring at room temperature, a 3:2 mixture of 2-fluoro-5-(methylthio)nitrobenzene and 2-chloro-5-(methylthio)nitrobenzene (1.39 g) was added. The mixture was stirred overnight at room temperature, poured into water and extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with ethyl acetate-hexane (1:6 to 1:4) as eluent. The eluted substance was recrystallized from ethyl acetate-hexane to give 0.60 g of the title compound as yellow crystals.
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