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

HRID 1626724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626724
[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]

Komponenten

8

Edukt 4

HCID 65578Oxalyl chlorideHCID 78878Methyl 2-amino-5-chlorobenzoateHCID 516892Sodium BicarbonateHCID 189451333-(Furan-3-yl)benzoic acid

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7acbd7cfee14498ba6699438d4cfee51
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785473B2

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