Sulfuric Acid → 2,6-Dichloro-4-methylbenzamide
Reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[C:4]#[N:5].S(=O)(=O)(O)[OH:13]>>[Cl:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[C:4]([NH2:5])=[O:13]Participants
3
Procedure
To stirred, cooled concentrated sulfuric acid (40 ml) was added in portions 2,6-dichloro-4-methylbenzonitrile (13.2 g, 71.0 mmol). The mixture was heated on a steam bath for 3 hours with occasional shaking, cooled, poured into ice-water, and extracted twice with dichloromethane. The combined extracts were washed with brine, dried over anhydrous magnesium sulfate, and evaporated under vacuum. The residue was chromatographed on a column of silica gel (390 g) eluted with 4:1 (v/v) dichloromethane-diethyl ether to provide 8.6 g (59%) of 2,6-dichloro-4-methylbenzamide, m.p. 101°-107° C.
Workup
- temperatureThe mixture was heated on a steam bath for 3 hours with occasional shaking
- temperaturecooled