Reaction #2336532

Reaction equation

Water

Thiophenol

potassium carbonate

DMF

→

title compound

Yield 52.0%

3,6-Bis(phenylthio) phthalonitrile

Yield 52.0%

Conditions

Workup

1. 1
   Filtrationthen filtered
2. 2
   OtherThe filter cake was purified by flash column chromatography (gradient elution 10%-30% ethyl acetate:isohexane)

Procedure

Thiophenol (11.75 g, 107 mmol), potassium carbonate (14.74 g, 107 mmol) and ditosylated dicyanohydroquinone (25.00 g, 53.0 mmol) in DMF (80 mL) were reacted as described above. Water (100 mL) was added and the mixture stirred for 1 hour then filtered. The filter cake was purified by flash column chromatography (gradient elution 10%-30% ethyl acetate:isohexane) to give the title compound as a yellow solid (5.53 g, 16.1 mmol, 52%). [Found: C, 69.6%; H, 3.5%; N, 8.2%; S, 18.3%; C20H12N2S2 requires C, 69.8%; H, 3.5%; N, 8.1%; S, 18.6%]; MS (EI+) 344 (M+, 100%).

Source