Thionyl Chloride → 3-Chloro-2-nitrobenzonitrile
Reaction equation
[Cl:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=O.S(Cl)(Cl)=O>CN(C=O)C>[Cl:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]#[N:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
A solution of 3-chloro-2-nitrobenzamide (step 1, 1.2 g, 4.9 mmol) in DMF (8 ml) was added thionyl chloride (2 ml, 24.8 mmol) in DMF (3 ml) dropwise at room temperature. The mixture was stirred at 120° C. for 2.5 h. The mixture was poured into ice-water and extracted with ethyl acetate (200 ml). The organic layer was washed with saturated aqueous NaHCO3 (100 ml), brine (100 ml), then dried (MgSO4), and concentrated. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (3:1/1:2) to give 1 g (quant.) of the title compound as pale yellow solids.
Workup
- extractionextracted with ethyl acetate (200 ml)
- washThe organic layer was washed with saturated aqueous NaHCO3 (100 ml), brine (100 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe residue was purified by flash chromatography
- washeluting with hexane/ethyl acetate (3:1/1:2)
Sources & evidence
- ORD record
- ord-c528c2872c09490099c5a63ed50aa2ff
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07479564B2
Reaction notes
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