Ethyl Acetate → N-[3-(3,4-dinitro-phenoxy)-phenyl]-acetamide

HRID 491634

Reaktionsgleichung

Reaktionsgleichung von HRID 491634
[N+:1]([C:4]1[CH:5]=[C:6](F)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-:3])=[O:2].[C:14]([NH:17][C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1)(=[O:16])[CH3:15].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[O:24][C:20]1[CH:19]=[C:18]([NH:17][C:14](=[O:16])[CH3:15])[CH:23]=[CH:22][CH:21]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 121243-HydroxyacetanilideHCID 2986753,4-Dinitrofluorobenzene

Produkt 1

HCID 86002098N-[3-(3,4-dinitro-phenoxy)-phenyl]-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a mixture of 3,4-dinitrofluorobenzene (1.0 g, 5.4 mmol, 1.0 eq.) and 3-acetamidophenol (0.8 g, 5.4 mmol, 1.0 eq.) in 10 mL of anhydrous DMF, K2CO3 (0.7 g, 5.4 mmol, 1.0 eq) was added. The reaction mixture was heated to 120° C. and stirred for 16 h. The mixture was cooled to RT and EtOAc was added (100 mL). After washing with H2O (100 mL), the organic layer was dried (MgSO4), filtered and concentrated. The resulting crude material was purified by column chromatography (20-100% EtOAc in hexanes) to obtain pure N-[3-(3,4-dinitro-phenoxy)-phenyl]-acetamide.

Aufarbeitung

  1. additionwas added
  2. temperatureThe mixture was cooled to RT
  3. washAfter washing with H2O (100 mL)
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude material was purified by column chromatography (20-100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-207a6e02ee8e4ede907d6463bba283b7
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531553B2

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