Divinyl sulfone → 4-(1,1-Dioxothiomorpholino)benzonitrile

Participants

Reaction Conditions

Reaction Steps

Aluminium trichloride (1.13 g, 8.46 mmol) was suspended in chlorobenzene (50 ml) at 0° C. Divinyl sulfone (850 μl, 8.46 mmol) was added followed by 4-aminobenzonitrile (1.0 g, 8.46 mmol). The mixture was allowed to reach room temperature and was then stirred at 130° C. for 90 hours. The reaction was cooled and diluted with CH2Cl2 (200 ml), water (150 ml) and MeOH (50 ml) before filtration. Filtered liquid was separated and the aqueous phase was extracted with CH2Cl2 (50 ml). Combined organics were dried over MgSO4 and evaporated. The crude product was purified by flash chromatography using pet.ether/EtOAc (1:1→0:1) as eluent to give 610 mg (30%) of the title compound as pale solids.

Provenance & Evidence