Hydrochloric Acid → 1-propyl-1H-imidazol-2-amine

HRID 1612315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1612315
C1(/C=[N:8]/[C:9]2[N:10]([CH2:14][CH2:15][CH3:16])[CH:11]=[CH:12][N:13]=2)C=CC=CC=1.Cl>>[CH2:14]([N:10]1[CH:11]=[CH:12][N:13]=[C:9]1[NH2:8])[CH2:15][CH3:16]

Komponenten

3

Edukt 2

HCID 313Hydrochloric AcidHCID 22147424(E)-1-phenyl-N-(1-propylimidazol-2-yl)methanimine

Produkt 1

HCID 221475261-propyl-1H-imidazol-2-amineAusbeute 56 %

Versuchsvorschrift

A mixture of N-[(1E)-phenylmethylidene]-1-propyl-1H-imidazol-2-amine (0.92 g, 4.31 mmol) and 6N HCl (25 mL) was heated at reflux for 2 h. After cooling to rt, the reaction was concentrated to a residue then taken up in 2M aqueous Na2CO3 and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude product was purified by column chromatography (Biotage, 40M) with CH2Cl2/MeOH/NH4OH (gradient, 950:47:3 to 900:90:10) to give 0.30 g (56%) of brown oil: 1H NMR (400 MHz, CDCl3) δ 6.63, 6.52, 4.00, 3.65, 1.75, 0.95; MS (ESI+) 126.7.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationthe reaction was concentrated to a residue
  4. extractionextracted with CH2Cl2
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (Biotage, 40M) with CH2Cl2/MeOH/NH4OH (gradient, 950:47:3 to 900:90:10)

Quellen und Nachweise

ORD-Eintrag
ord-2de3aff44d8c4e998845e365522a33af
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06992087B2

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