Reaction #2336533

Reaction equation

2-Methylthiophenol

potassium carbonate

DMF

→

title compound

Yield 42.0%

3,6-Bis(2′-methylphenylthio) phthalonitrile

Yield 42.0%

Conditions

Workup

1. 1
   OtherThe mixture was isolated
2. 2
   Otherto give a yellow oil
3. 3
   OtherThe material was purified by flash column chromatography (eluting 10% ethyl acetate:isohexane)

Procedure

2-Methylthiophenol (10.60 g, 85.5 mmol), potassium carbonate (11.82 g, 82.0 mmol) and ditosylated dicyanohydroquinone (20.00 g, 42.7 mmol) in DMF (75 mL) were reacted as described above. The mixture was isolated as described above to give a yellow oil. The material was purified by flash column chromatography (eluting 10% ethyl acetate:isohexane) to give the title compound as a yellow solid (8.85 g, 23.8 mmol, 42%). [Found: C, 70.7%; H, 4.6%; N, 7.5%; S, 17.2%; C22H16N2S2 requires C, 70.9%; H, 4.3%; N, 7.5%; S, 17.2%]; MS (EI+) 372 (M+, 100%), 357 (M-CH3, 8), 339 (20).

Source