Ethyl Acetate → Methyl {p-{5-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-2-nitroanilino}phenoxy}acetate

HRID 21519

Reaktionsgleichung

Reaktionsgleichung von HRID 21519
F[C:2]1[CH:3]=[C:4]([O:11][C:12]2[CH:17]=[C:16]([F:18])[C:15]([C:19]([F:22])([F:21])[F:20])=[C:14]([Cl:23])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[NH2:24][C:25]1[CH:36]=[CH:35][C:28]([O:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.[Cl-].[Na+].O>[Cl:23][C:14]1[CH:13]=[C:12]([O:11][C:4]2[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH:3]=2)[NH:24][C:25]2[CH:26]=[CH:27][C:28]([O:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:35][CH:36]=2)[CH:17]=[C:16]([F:18])[C:15]=1[C:19]([F:20])([F:22])[F:21]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 6422115Methyl(4-aminophenoxy)acetateHCID 867487172-Chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl 3-fluoro-4-nitrophenyl ether

Produkt 1

HCID 86748716Methyl {p-{5-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-2-nitroanilino}phenoxy}acetateAusbeute 19,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2-chloro-α,α,α,6-tetrafluoro-p-tolyl 3-fluoro-4-nitrophenyl ether (2.1 g, 0.006 mol), methyl (p-aminophenoxy)acetate (2.7 g, 0.015 mol) and potassium carbonate (2.0 g, 0,015 mol) in N,N-dimethyl formamide is stirred at 80° C. for 18 hours, cooled to room temperature, poured into brine and extracted with ethyl acetate. The organic extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Flash chromatography of the residue using silica gel and a 20% ethyl acetate in hexanes solution gives the title product as a red oil (0.6 g) which is identified by 1HNMR and 13CNMR spectral analyses.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washis washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue

Quellen und Nachweise

ORD-Eintrag
ord-83e80843e5f64dcf9c75d52225a97513
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424280

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