Sodium hydride → 2-(4-Chloropyridin-2-yloxy)-4,5-dichlorobenzenamine

HRID 588789

Reaktionsgleichung

Reaktionsgleichung von HRID 588789
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[OH:10].[H-].[Na+].[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16](F)[CH:15]=1>C1COCC1>[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([O:10][C:3]2[CH:4]=[C:5]([Cl:9])[C:6]([Cl:8])=[CH:7][C:2]=2[NH2:1])[CH:15]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 27628394-Chloro-2-fluoropyridineHCID 30154152-Amino-4,5-dichlorophenol

Produkt 1

HCID 1176071602-(4-Chloropyridin-2-yloxy)-4,5-dichlorobenzenamineAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-4,5-dichlorophenol (1.5 g, 8.47 mmol) in THF (20 mL) at 0° C., NaH (60% dispersed in oil, 373 mg, 9.33 mmol) was added and the resulting mixture was stirred for 20 min. To this mixture, 4-chloro-2-fluoropyridine (1.67 g, 12.7 mmol) was added and the resulting mixture was stirred at reflux under argon for 15 h. The mixture was allowed to cool to room temperature and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1 to 10:1) to afford the desired product (1.1 g, 45% yield). ESI-MS m/z: 287.0 [M−H]−.

Aufarbeitung

  1. stirringthe resulting mixture was stirred
  2. temperatureat reflux under argon for 15 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-72729ac48648442da4a5385bfc265a6b
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227978B2

Verknüpfte Notizen

Wird geladen…