Water → (4-Methoxy-phenyl)-(2-methyl-6-nitro-phenyl)amine

HRID 2092933Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2092933
F[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.C(C)(C)C([O-])=O.[K+].O>CS(C)=O>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=2[CH3:11])=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7732P-AnisidineHCID 134709572-Fluoro-1-methyl-3-nitrobenzeneHCID 23677462Potassium isobutyrate

Produkt 1

HCID 67528647(4-Methoxy-phenyl)-(2-methyl-6-nitro-phenyl)amineAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 50 g of 2-fluoro-3-nitrotoluene in 1.1 L of DMSO are added at room temperature 59.5 g of para-anisidine (1.5 equivalents). After 5 minutes of stirring at room temperature, 57.9 g of potassium tert-butanoate (1.6 equivalents) are added to the reaction medium and the whole is heated to 110° C. for 1 hour. The reaction medium is directly hydrolyzed by adding 1 L of ice and water and then the aqueous phase is extracted several times with ethyl acetate. The organic phases are collected, dried on sodium sulphate, filtered and then dry concentrated. The raw product is chromatographed on silica gel (ether/cyclohexane:0/100, 5/95 and then 20/80) in order to provide 34.95 g of the expected compound as a dark red solid.

Aufarbeitung

  1. temperaturethe whole is heated to 110° C. for 1 hour
  2. extractionthe aqueous phase is extracted several times with ethyl acetate
  3. customThe organic phases are collected
  4. customdried on sodium sulphate
  5. filtrationfiltered
  6. customdry
  7. concentrationconcentrated
  8. customThe raw product is chromatographed on silica gel (ether/cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-c05fb29caece430f87dc0ce986753941
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440833B2

Notizen zur Reaktion

Wird geladen…