Thionyl Chloride → Benzoic acid, 3-chloro-5-cyano-, methyl ester
Reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([Cl:14])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])=O.S(Cl)(Cl)=O>CN(C)C=O>[Cl:14][C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([C:2]#[N:1])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
(Step 1) To a solution of methyl 3-(aminocarbonyl)-5-chlorobenzoate (2.2 g) in N,N-dimethylformamide (15 ml) was added thionyl chloride (2 ml) at 0° C., and the mixture was stirred at 80° C. for 1 hr. The reaction solution was quenched with ice and extracted with ethyl acetate. The extract was washed with aqueous sodium hydrogen carbonate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=1:1) to give methyl 3-chloro-5-cyanobenzoate (1.15 g) as a white solid.
Workup
- customThe reaction solution was quenched with ice
- extractionextracted with ethyl acetate
- washThe extract was washed with aqueous sodium hydrogen carbonate solution
- dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- additionthe obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=1:1)
Sources & evidence
- ORD record
- ord-c0f803a604514148969246b33a2495ca
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470859B2
Reaction notes
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