Hydrochloric Acid → (E)-1-(4-Methylpyrid-2-yl)-2-styryl-1H-benzimidazole hydrochloride

HRID 50871

Reaction equation

HRID 50871 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.F[C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.[ClH:49]>CO>[ClH:49].[CH3:25][C:23]1[CH:22]=[CH:21][N:20]=[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)[CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2429652-(2-Phenylethenyl)-1h-benzimidazoleHCID 27374032-Fluoro-4-methylpyridineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole

Product 1

HCID 22736699(E)-1-(4-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-fluoro-4-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: 358.68; mp: 221.0-222.5° C.; 1H-NMR (DMSO) δ: 8.66 (1H, d, J=5.1 Hz), 8.22-8.15 (1H, m), 7.86 (1H, d, J=7.7 Hz), 7.71-7.66 (3H, m), 7.59-7.44 (7H, m), 7.20 (1H, d, J=16.1 Hz), 2.53 (3H, s).

Workup

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

Sources & evidence

ORD record
ord-e7563a17df69493da72aa3c4147489d9
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Linked notes

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