Hydrochloric Acid → (E)-1-(3-Methylpyrid-2-yl)-2-styryl-1H-benzimidazole hydrochloride

HRID 50868

Reaction equation

HRID 50868 reaction equation
[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[C:24]([CH3:25])=[CH:23][CH:22]=[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:24]1[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]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 876032-Chloro-3-methylpyridineHCID 2429652-(2-Phenylethenyl)-1h-benzimidazoleHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole

Product 1

HCID 22736672(E)-1-(3-Methylpyrid-2-yl)-2-styryl-1H-benzimidazole hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Free base of the titled compound was prepared from 2-styryl-1H-benzimidazole and 2-Chloro-3-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/n-hexane to give the titled compound. MW: 347.85; mp: 226.0-228.0° C.; 1H-NMR (DMSO-d6) δ: 8.66-8.62 (1H, m), 8.21-8.14 (2H, m), 7.91 (1H, d, J=8.1 Hz), 7.76 (1H, dd, J=7.7, 4.8 Hz), 7.68-7.60 (2H, m), 7.60-7.54 (1H, m), 7.50-7.43 (4H, m), 7.26 (1H, d, J=8.1 Hz), 6.89 (1H, d, J=16.5 Hz), 2.12 (3H,s).

Workup

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

Sources & evidence

ORD record
ord-7770019e73914e6aad83f240ef6dbf2c
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Linked notes

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