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

HRID 2249349Notes

Reaction equation

HRID 2249349 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

5

Reactant 3

HCID 6228DimethylformamideHCID 78114-MethylbenzenethiolHCID 11430Potassium Carbonate

Product 2

HCID 78922-MethylpentaneHCID 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).

Workup

  1. customThe mixture was isolated
  2. customto give a yellow solid
  3. customThe solid was purified by flash column chromatography (
  4. washgradient elution

Sources & evidence

ORD record
ord-64b12cad1be34755b72490c9202d3f0a
Source dataset
uspto-grants-2008_01
Patent number
US07314511B2

Reaction notes

Loading…