Acetic Acid → 3-(4-Amino-2-fluorobenzyl)-1,3-oxazolidin-2-one

HRID 241756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241756
[F:1][C:2]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:9][CH2:8][O:7][C:6]1=[O:10].C(O)(=O)C.[OH-].[Na+]>C(O)C.[Fe]>[NH2:15][C:13]1[CH:12]=[CH:11][C:3]([CH2:4][N:5]2[CH2:9][CH2:8][O:7][C:6]2=[O:10])=[C:2]([F:1])[CH:14]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 666368043-(2-Fluoro-4-nitrobenzyl)-1,3-oxazolidin-2-one

Produkt 1

HCID 647676883-(4-Amino-2-fluorobenzyl)-1,3-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of the compound obtained in Step B (10.37 mmoles) in ethanol (25 ml) there are added 122 microliters of acetic acid. The solution is heated at reflux and stirred for 10 minutes. Powdered iron (2.08 g) and 75 mg of FeCl3.6H2O are added. After stiffing for 2 hours at reflux, the mixture is brought to ambient temperature and then concentrated to dryness. 50 ml of water are added to the residue obtained, and the pH is made alkaline using sodium hydroxide. The solution is extracted 4 times with AcOEt. The organic phases are combined and washed with saturated aqueous NaCl solution and then dried with MgSO4. After filtration, the organic phase is evaporated to dryness to yield the title product, which is used directly in the next Step.

Aufarbeitung

  1. temperatureThe solution is heated
  2. temperatureat reflux
  3. waitAfter stiffing for 2 hours
  4. temperatureat reflux
  5. customis brought to ambient temperature
  6. concentrationconcentrated to dryness
  7. addition50 ml of water are added to the residue
  8. customobtained
  9. extractionThe solution is extracted 4 times with AcOEt
  10. washwashed with saturated aqueous NaCl solution
  11. dry with materialdried with MgSO4
  12. filtrationAfter filtration
  13. customthe organic phase is evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e327438c04dd470a92d324aa793811f7
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653073B2

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