Hydrochloric Acid → (E)-1-(5-Methylpyrid-2-yl)-2-styryl-1H-benzimidazole hydrochloride

HRID 50872

Reaktionsgleichung

Reaktionsgleichung von HRID 50872
[CH:1]([C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.Cl>CO>[ClH:18].[CH3:25][C:22]1[CH:23]=[CH:24][C:19]([N:13]2[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[N:10]=[C:9]2/[CH:1]=[CH:2]/[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[N:20][CH:21]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 2429652-(2-Phenylethenyl)-1h-benzimidazoleHCID 5813932-Chloro-5-methyl-pyridineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole

Produkt 1

HCID 22736693(E)-1-(5-Methylpyrid-2-yl)-2-styryl-1H-benzimidazole hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Free base of the titled compound was prepared from 2-styryl-1H-benzimidazole and 2-Chloro-5-methylpyridine 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 ethyl acetate-hexane to give the titled compound. MW: 347.85; mp: 245.0-247.0° C.; 1H-NMR (DMSO-d6) δ: 8.66 (1H, d, J=1.8 Hz), 8.19 (1H, d, J=16.1 Hz), 8.08 (1H, dd, J=8.1, 2.1 Hz), 7.87 (1H, d, J=8.8 Hz), 7.76 (1H, d, J=8.1 Hz), 7.71-7.66 (2H, m), 7.57-7.52 (2H, m), 7.49-7.44 (4H, m), 7.19 (1H, d, J=16.1 Hz), 2.50 (3H, s).

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. customThe residue was recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-32f27ba2bba54cb4a6d3453dbd85a274
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713482B2

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