O-Xylene → HCID 14118983, compound

Participants

Reaction Steps

2-(2-Aminophenylthio)-5-nitrobenzonitrile (8.5 g, 25 mmol) was dissolved in a mixture of glacial acetic acid (80 ml), concentrated sulphuric acid (100 ml) and water (80 ml) and then heated under reflux for 6 hours. The cooled mixture was added to ice water (500 ml) and brought to pH 4 by addition of 10N aqueous sodium hydroxide. Extraction with dichloromethane followed by filtration, drying (sodium sulphate) and evaporation of the organic layer afforded a residue which was put into xylene (500 ml) and refluxed for 15 hours with azeotropic removal of water. On cooling a brown powder deposited which was filtered off and purified by chromatography on silica gel eluting with 1:1 v/v ethyl acetate-hexane. Recrystallisation from ethanol gave the product as a greyish powder (2.80 g, m/s, M+ =272).

Provenance & Evidence