Water → N-(2,5-Difluoro-4-nitrophenyl)acetamide

HRID 1030986

Reaktionsgleichung

Reaktionsgleichung von HRID 1030986
[F:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([F:12])=[CH:5][C:3]=1[NH2:4].[C:13](OC(=O)C)(=[O:15])[CH3:14].O>C(Cl)Cl.S(=O)(=O)(O)O.CN(C1C=CC=CN=1)C>[F:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([F:12])=[CH:5][C:3]=1[NH:4][C:13](=[O:15])[CH3:14]

Komponenten

7

Edukt 3

HCID 962WaterHCID 7918Acetic Anhydride2×HCID 2359302,5-Difluoro-4-nitroaniline

Produkt 1

HCID 14624893N-(2,5-Difluoro-4-nitrophenyl)acetamideAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1118Sulfuric AcidKatalysatorHCID 218852-DimethylaminopyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 6.0 g (0.034 mole) of 2,5-difluoro-4-nitroaniline, 6.5 g (0.064 mole) of acetic anhydride, and approximately 0.1 g (0.0008 mole) of dimethylaminopyridine in 300 ml of methylene chloride was stirred and heated at reflux for two hours. The reaction mixture was allowed to cool and stir at room temperature for approximately 18 hours. The solvent was removed from the mixture by distillation under reduced pressure, leaving a residue. To this residue was added 32.5 g (0.318 mole) of acetic anhydride and several drops of concentrated sulfuric acid. This mixture was stirred at room temperature for approximately 18 hours. Approximately 300 ml of water was added to the mixture causing a vigorous exotherm and a solid to form. This solid was collected by filtration. The filter cake was washed with water and was dried under reduced pressure to yield 6.5 g of N-(2,5-difluoro-4-nitrophenyl)acetamide. The nmr spectrum was consistent with the proposed structure.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for two hours
  3. temperatureto cool
  4. stirringstir at room temperature for approximately 18 hours
  5. customThe solvent was removed from the mixture by distillation under reduced pressure
  6. customleaving a residue
  7. stirringThis mixture was stirred at room temperature for approximately 18 hours
  8. customa solid to form
  9. filtrationThis solid was collected by filtration
  10. washThe filter cake was washed with water
  11. customwas dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e03af009080341838c315f5351746e77
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05108486

Verknüpfte Notizen

Wird geladen…