Reaction #2336531

Reaction equation

4-Methylthiophenol

potassium carbonate

DMF

→

isohexane

title compound

Yield 52.0%

3,6-Bis(4′-methylphenylthio) phthalonitrile

Yield 52.0%

Conditions

Workup

1. 1
   OtherThe mixture was isolated
2. 2
   Otherto give a yellow solid
3. 3
   OtherThe solid was purified by flash column chromatography (
4. 4
   Washgradient elution

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).

Source