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

HRID 382540
Notes
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Reaction equation

HRID 382540 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887
Methanol
Solvent

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/n-hexane to give the titled compound.

Workup

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

Sources & evidence

ORD record
ord-b40bf3b11c6f4d01a610b87774c36c88
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06310079B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes