Hydrochloric Acid → (E)-4-Methyl-1-(2-pyridyl)-2-styryl-1H-benzimidazole hydrochloride

HRID 50915

Reaktionsgleichung

Reaktionsgleichung von HRID 50915
[CH3:1][C:2]1[C:10]2[N:9]=[C:8](/[CH:11]=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.F[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.[ClH:49]>CO>[ClH:49].[CH3:1][C:2]1[C:10]2[N:9]=[C:8](/[CH:11]=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 97462-FluoropyridineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 22736633(E)-4-methyl-2-styryl-1H-benzimidazole

Produkt 1

HCID 22736702(E)-4-Methyl-1-(2-pyridyl)-2-styryl-1H-benzimidazole hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Free base of the titled compound was prepared from (E)-4-methyl-2-styryl-1H-benzimidazole and 2-fluoropyridine according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method B). The free base was treated with a 10% methanol solution of hydrogen chloride and concentrated to dryness. The residue was recrystallized from 2-propanol/isopropyl ether to give the titled compound. MW: 347.85; mp: 218.0-225.0° C.; 1H-NMR (DMSO) δ: 8.85-8.80 (1H, m), 8.45 (1H, d, J=16.1 Hz), 8.27 (1H, ddd, J=7.7,7.7, 1.5 Hz), 7.86 (1H, d, J=7.7 Hz), 7.77 (1H, dd, J=7.7, 4.5 Hz), 7.70-7.65 (2H, m), 7.48-7.42 (3H, m), 7.41-7.33 (3H, m), 7.17 (1H, d, J=16.1 Hz), 2.76 (3H, s).

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. customThe residue was recrystallized from 2-propanol/isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-6b5e8b86574d440489da0de69a6b44d0
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713482B2

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