Dimethylformamide → 3,6-Bis[(4-methylphenyl)sulfanyl]benzene-1,2-dicarbonitrile

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C[N:16]([CH:18]=O)C>>[CH3:5][CH2:4][CH2:3][CH:2]([CH3:7])[CH3:1].[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:2]2[CH:7]=[CH:6][C:5]([S:8][C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)=[C:4]([C:18]#[N:16])[C:3]=2[C:18]#[N:16])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 78114-Methylbenzenethiol

HCID 11430Potassium Carbonate

Product 2

HCID 78922-Methylpentane

HCID 596388603,6-Bis[(4-methylphenyl)sulfanyl]benzene-1,2-dicarbonitrileYield 52%

Procedure

4-Methylthiophenol (3.41 g, 27.5 mmol), potassium carbonate (3.80 g, 27.5 mmol) and ditosylated dicyanohydroquinone (i.e. product A) (5.00 g, 10.7 mmol) in DMF (40 mL) were reacted as described above. The mixture was isolated as described above to give a yellow solid. The solid was purified by flash column chromatography (gradient elution: 5%-10%-30% ethyl acetate:isohexane, finally dichloromethane) to give the title compound as a yellow solid (2.07 g, 52%). [Found: C, 69.9%; H, 4.4%; N, 7.3%; S, 16.9%; C22H16N2S2 requires C, 70.9%, H, 4.3%, N, 7.5%, S, 17.2%]; MS (EI+) 372 (M+, 100%), 357 (M-CH3, 5%), 123 (CH3C6H4S, 15), 91 (CH3C6H4, 15).