Oxalic Acid → (E)-1-(2-Pyridyl)-2-[2-(3-pyridyl)ethenyl]-1H-benzimidazole oxalate

HRID 382587

Reaction equation

HRID 382587 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[N:3]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=1.Cl.Cl.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CN=1.[C:50]([OH:55])(=[O:54])[C:51]([OH:53])=[O:52]>CO>[C:50]([OH:55])(=[O:54])[C:51]([OH:53])=[O:52].[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[N:6]1[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[N:3]=[C:2]1/[CH:1]=[CH:23]/[C:19]1[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 103713-PyridinecarboxaldehydeHCID 227366432-Methyl-1-(pyridin-2-yl)-1H-benzimidazoleHCID 22736657(E)-1-(2-Pyridyl)-2-[2-(2-pyridyl)ethenyl]-1H-benzimidazole dihydrochloride

Product 1

HCID 22736735(E)-1-(2-Pyridyl)-2-[2-(3-pyridyl)ethenyl]-1H-benzimidazole oxalate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Free base of the titled compound was prepared from 2-methyl-1-(2-pyridyl)-1H-benzimidazole and pyridine-3-carboxaldehyde according to the preparation of (E)-1-(2-pyridyl)-2-[2-(2-pyridyl)ethenyl]-1H-benzimidazole dihydrochloride (Example 44). The free base and oxalic acid were dissolved into MeOH. Concentration and recrystallization from ethyl MeOH/EtOH yielded the titled compound.

Workup

  1. concentrationConcentration and recrystallization from ethyl MeOH/EtOH

Sources & evidence

ORD record
ord-0fc7c89e3ade461b9d7d2308e376abb1
Source dataset
uspto-grants-2001_10
Patent number
US06310079B1

Linked notes

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