Oxalyl chloride → Methyl 5-chloro-2-({[3-(furan-3-yl)phenyl]carbonyl}amino)benzoate

HRID 1626724Notes

Reaction equation

HRID 1626724 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9]([OH:11])=O)=[CH:2]1.C(Cl)(=O)C(Cl)=O.[NH2:21][C:22]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25].C(=O)([O-])O.[Na+]>C1COCC1.CC(N(C)C)=O.CN(C)C=O>[Cl:32][C:29]1[CH:30]=[CH:31][C:22]([NH:21][C:9]([C:8]2[CH:12]=[CH:13][CH:14]=[C:6]([C:3]3[CH:4]=[CH:5][O:1][CH:2]=3)[CH:7]=2)=[O:11])=[C:23]([CH:28]=1)[C:24]([O:26][CH3:27])=[O:25]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 78878Methyl 2-amino-5-chlorobenzoateHCID 516892Sodium BicarbonateHCID 18945133HCID 18945133, compound

Product 1

HCID 66680385Methyl 5-chloro-2-({[3-(furan-3-yl)phenyl]carbonyl}amino)benzoateYield 67%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

0.50 g (2.7 mmol) of 3-(furan-3-yl)benzoic acid, a catalytic amount of N,N-dimethylformamide (DMF), 0.78 g (3.7 mmol) of oxalyl chloride were stirred at 0° C. for 30 minutes in 10 mL of THF. Thereafter, the solvent was distilled off under reduced pressure. 0.49 g (2.7 mmol) of methyl 2-amino-5-chlorobenzoate and 5 mL of DMAc were added to the obtained residue at 0° C., and the mixture was stirred at room temperature for 0.5 hours. After the completion of the reaction, an aqueous sodium hydrogen carbonate solution was added. The precipitated solids were collected by filtration, followed by washing with water and IPE, thereby giving 0.63 g of methyl 5-chloro-2-({[3-(furan-3-yl)phenyl]carbonyl}amino)benzoate (yield: 67%).

Workup

  1. distillationThereafter, the solvent was distilled off under reduced pressure
  2. customAfter the completion of the reaction
  3. filtrationThe precipitated solids were collected by filtration
  4. washby washing with water and IPE

Sources & evidence

ORD record
ord-7acbd7cfee14498ba6699438d4cfee51
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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