Reaktion #2336533

ord-d894e478ca4346788f845d2f4943a11e

Reaktionsgleichung

Cc1ccccc1S
2-Methylthiophenol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CN(C)C=O
DMF
Cc1ccccc1Sc1ccc(Sc2ccccc2C)c(C#N)c1C#N
title compound
Ausbeute 42.0%
Cc1ccccc1Sc1ccc(Sc2ccccc2C)c(C#N)c1C#N
3,6-Bis(2′-methylphenylthio) phthalonitrile
Ausbeute 42.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07314511B2uspto-grants-2008_01