Hydrochloric Acid → (E)-2-(3-Methyl-1-butenyl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

HRID 50900Notes

Reaction equation

HRID 50900 reaction equation
N1C=CC=CC=1NC1C=CC=CC=1N.CC(C)C=CC([Cl:21])=O.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[C:30]1/[CH:38]=[CH:39]/[C:40]1[CH:45]=CC=C[CH:41]=1.Cl>CO>[ClH:21].[CH3:41][CH:40]([CH3:45])/[CH:39]=[CH:38]/[C:30]1[N:29]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 541700634-Methyl-2-pentenoyl chloride

Product 1

HCID 22736743(E)-2-(3-Methyl-1-butenyl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and 4-methyl-2-pentenoyl chloride (Yamada, T.; Takashima, K.; Miyazawa, T.; Kuwata, S.; Watanabe, H. Bull. Chem. Soc. Jpn. 1978, 51, 878) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). 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: 299.81; mp: 140.0-141.0° C.; 1H-NMR (DMSO) δ: 8.81-8.79 (1H, m), 8.25 (1H, td, J=8.1, 1.8 Hz), 7.85-7.79 (2H, m), 7.77-7.71 (1H, m), 7.56-7.45 (3H, m), 7.31 (1H, dd, J=16.1, 7.0 Hz), 6.47-6.40 (1H, m), 2.75-2.55 (1H, m), 1.05 (6H, d, J=7.0 Hz).

Workup

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

Sources & evidence

ORD record
ord-617e8899272b4ca4b27e428302f18a0d
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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