Water → (E)-1-(6-Methoxypyridin-2-yl)-2-styryl-1H-benzimidazole hydrochloride

HRID 50876

Reaktionsgleichung

Reaktionsgleichung von HRID 50876
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[CH:4][CH:3]=1.C[CH2:26][O-:27].[Na+].O>CO.C1(C)C=CC=CC=1>[ClH:1].[CH3:26][O:27][C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 22736737(E)-1-(6-chloropyridin-2-yl)-2-styryl-1H-benzimidazole

Produkt 1

HCID 22736731(E)-1-(6-Methoxypyridin-2-yl)-2-styryl-1H-benzimidazole hydrochlorideAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

According to the literature procedure (Trecourt, F.; Mallet, M.; Mongin, O,.; Queguiner, G. J. Org. Chem. 1994, 59, 6173.), a solution of (E)-1-(6-Chloropyridin-2-yl)-2-styryl-1H-benzimidazole (145 mg, 0.44 mmol), 28% NaOEt in MeOH (3 ml) and toluene (5 ml) was maintained at room temperature for 2 h then heated under reflux condition for 1 h. To this solution, water (1 ml) was added and it was concentrated by evaporator. To this residue , water (5 ml) was added and the whole was extracted with CH2Cl2 (2×15 ml). Combined organic layer was dried (magnesium sulfate) and filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, 20 g; n-hexane/ethyl acetate (5/1)) to afford the desired compound (35 mg, 24%). The free base was treated with a 10% methanol solution of hydrogen chloride and concentrated to dryness. The residue was recrystallized from ethyl acetate/n-hexane to give the titled compound. MW: 363.85; mp: 199.0-200.0° C.; 1H-NMR (DMSO) δ: 8.15-8.08 (2H, m), 7.85 (1H, d, J=8.1 Hz), 7.74-7.66 (3H, m), 7.56-7.20 (6H, m), 7.15 (1H, d, J=8.4 Hz), 702-7.00 (1H, m), 3.90 (3H, s).

Aufarbeitung

  1. temperaturethen heated
  2. temperatureunder reflux condition for 1 h
  3. concentrationit was concentrated by evaporator
  4. additionTo this residue , water (5 ml) was added
  5. extractionthe whole was extracted with CH2Cl2 (2×15 ml)
  6. dry with materialCombined organic layer was dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe residue was purified by column chromatography (silica gel, 20 g; n-hexane/ethyl acetate (5/1))

Quellen und Nachweise

ORD-Eintrag
ord-ff525ce8cef144c8b7ca725af7f8ab01
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713482B2

Verknüpfte Notizen

Wird geladen…