[N+]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[C:6]#[N:7])([O-])=O.C([O-])([O-])=O.[K+].[K+].[CH3:21][C:22]1[CH:23]=[C:24]([SH:29])[CH:25]=[C:26]([CH3:28])[CH:27]=1.O>CN(C=O)C>[CH3:21][C:22]1[CH:23]=[C:24]([S:29][C:4]2[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=2[C:6]#[N:7])[CH:25]=[C:26]([CH3:28])[CH:27]=1A mixture of 2,6-dinitrobenzonitrile (1.4 g 7.2 mmol) and K2CO3 (1.1 g, 7.9 mmol) in 10 ml of DMF was chilled to 0° C. A solution of 3,5-dimethylthiophenol (1.1 g 0.0079 mmol) in 10 ml of DMF, was added dropwise over 30 min with stirring under nitrogen. After stirring an additional 30 min, the reaction mixture was poured into 150 ml of water and stirred for 1 hr. The solid was collected by vacuum filtration. Chromatography on silica gel (flash; Hex/EtOAc 1:1) provided 1.64 g (80%) of 2-[(3,5-dimethylphenyl)thio]-6-nitrobenzonitrile: mp 155°-156° C.
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