HCID 23444980, Verbindung → 1-(3,4-dichloro-phenyl)-1H-imidazole-4-carbaldehyde

HRID 433589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 433589
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][OH:15])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]>C1COCC1.O.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH:14]=[O:15])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

5

Edukt 1

HCID 23444980HCID 23444980, Verbindung

Produkt 1

HCID 234451021-(3,4-dichloro-phenyl)-1H-imidazole-4-carbaldehydeAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418406HCID 178418406, VerbindungKatalysator2×HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of [1-(3,4-dichloro-phenyl)-1H-imidazol-4-yl]-methanol (10.8 g, 44.3 mmol) in a mixture of THF (270 ml) and H2O (30 ml) was treated with manganese(IV) oxide (5 g, 57.5 mmol) and the mixture was refluxed for 4 h. A second portion of manganese(IV) oxide (1.5 g) was added and reflux continued for 1.5 h. The mixture was filtered over Celite, and the residue was washed with MeOH. Toluene was added to the filtrate, and the H2O was removed azeotropically. The brown residue was taken up in CH2Cl2 and upon standing white crystals formed. Filtration afforded 1-(3,4-dichloro-phenyl)-1H-imidazole-4-carbaldehyde (2.5 g, 25%). MS: m/e=240.0 (M+).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 4 h
  2. temperaturereflux
  3. filtrationThe mixture was filtered over Celite
  4. washthe residue was washed with MeOH
  5. additionToluene was added to the filtrate
  6. customthe H2O was removed azeotropically
  7. customformed
  8. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-3aa0899d661c43edbead54ca0c6dcc13
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06667335B2

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