Nitric Acid → (1-Ethyl-1H-imidazol-5-yl)methanol

HRID 856770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 856770
[N+]([O-])(O)=O.N([O-])=O.[Na+].[CH2:9]([N:11]1[C:15]([CH2:16][OH:17])=[CH:14][N:13]=[C:12]1S)[CH3:10].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:9]([N:11]1[C:15]([CH2:16][OH:17])=[CH:14][N:13]=[CH:12]1)[CH3:10]

Komponenten

6

Edukt 4

HCID 944Nitric AcidHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 178462793HCID 178462793, Verbindung

Produkt 1

HCID 22988641(1-Ethyl-1H-imidazol-5-yl)methanolAusbeute 69,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 5.0M nitric acid (102 ml) was added sodium nitrite (314 mg), and 1-ethyl-5-hydroxymethyl-2-mercaptoimidazole (18.0 g) was added by portions to the mixture at 0° C. The mixture was allowed to be at room temperature and the mixture was stirred for 2 hours, and water (100 ml) was added to the mixture. The mixture was neutralized with potassium carbonate at 0° C., and the solvent was distilled off under reduced pressure. Ethanol was added to the mixture, and the insolubles were filtered off, and the solvent was distilled off under reduced pressure. To the obtained residue was added methanol-ethyl acetate, and basic silica gel was added to the mixture. This mixture was purified by basic silica gel column chromatography (methanol-ethyl acetate=1:8) to obtain solid, which was recrystallized from diisopropyl ether-ethyl acetate, to give 1-ethyl-5-hydroxymethylimidazole (10.0 g) as brown crystals.

Aufarbeitung

  1. additionwas added by portions to the mixture at 0° C
  2. customto be at room temperature
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionEthanol was added to the mixture
  5. filtrationthe insolubles were filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionTo the obtained residue was added methanol-ethyl acetate, and basic silica gel
  8. additionwas added to the mixture
  9. customThis mixture was purified by basic silica gel column chromatography (methanol-ethyl acetate=1:8)
  10. customto obtain solid, which
  11. customwas recrystallized from diisopropyl ether-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-11bb96415fcb4e09b064f60a97484933
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262185B2

Notizen zur Reaktion

Wird geladen…