Pyridine → Methyl 3-chloro-4-{[(4-nitrophenoxy)carbonyl]amino}benzoate

HRID 1691667

Reaktionsgleichung

Reaktionsgleichung von HRID 1691667
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].N1C=CC=CC=1.[NH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[Cl:31]>ClCCl>[Cl:31][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][C:21]=1[NH:20][C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3])[C:25]([O:27][CH3:28])=[O:26]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 1515284Methyl 4-Amino-3-chlorobenzoate

Produkt 1

HCID 59178754Methyl 3-chloro-4-{[(4-nitrophenoxy)carbonyl]amino}benzoateAusbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5.43 g of 4-nitrophenyl chloroformate in 100 mL of dichloromethane was added 2.4 mL of pyridine under ice-cooling, and 5 g of methyl 4-amino-3-chlorobenzoate was added to the obtained mixture, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added to the residue, followed by washing with 1 M hydrochloric acid, water, a saturated aqueous sodium hydrogen carbonate solution, water, and a saturated aqueous sodium chloride solution in this order. The organic layer was dried over anhydrous sodium sulfate, and after filtration, the filtrate was concentrated under reduced pressure. The obtained solid was dissolved in 200 mL of toluene under heating, and left to be cooled to room temperature, and further cooled in an ice bath. The precipitated solid was collected by filtration, and dried under reduced pressure to obtain 5.59 g of methyl 3-chloro-4-{[(4-nitrophenoxy)carbonyl]amino}benzoate as a white solid.

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
  3. additionwas added to the residue
  4. washby washing with 1 M hydrochloric acid, water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationafter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. dissolutionThe obtained solid was dissolved in 200 mL of toluene
  9. temperatureunder heating
  10. waitleft
  11. temperatureto be cooled to room temperature
  12. temperaturefurther cooled in an ice bath
  13. filtrationThe precipitated solid was collected by filtration
  14. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6a46a0be34bb463eb4e4a66bd4d312c9
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153658B2

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