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

HRID 382589

Reaction equation

HRID 382589 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.[NH:17]1[CH:21]=[CH:20][N:19]=[C:18]1[CH:22]=O.Cl.Cl.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CN=1.[C:49]([OH:54])(=[O:53])[C:50]([OH:52])=[O:51]>CO>[C:49]([OH:54])(=[O:53])[C:50]([OH:52])=[O:51].[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:22]/[C:18]1[NH:17][CH:21]=[CH:20][N:19]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 249551H-imidazole-2-carbaldehydeHCID 227366432-Methyl-1-(pyridin-2-yl)-1H-benzimidazoleHCID 22736657(E)-1-(2-Pyridyl)-2-[2-(2-pyridyl)ethenyl]-1H-benzimidazole dihydrochloride

Product 1

HCID 135709103(E)-1-(2-Pyridyl)-2-[2-(2-imidazolyl)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 2-imidazolcarboxaldehyde 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 EtOH/n-hexane yielded the titled compound.

Workup

  1. concentrationConcentration and recrystallization from ethyl EtOH/n-hexane

Sources & evidence

ORD record
ord-81fc12cce33e49d68cd71457f6b76a7d
Source dataset
uspto-grants-2001_10
Patent number
US06310079B1

Linked notes

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