Oxalic Acid → (E)-2-(3-Methyl-1-butenyl)-5-methoxy-1-(2-pyridyl)-1H-benzimidazole oxalate

HRID 382580Notes

Reaction equation

HRID 382580 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[C:5]([NH2:16])[CH:4]=1.[CH3:17][CH:18]([CH3:24])/[CH:19]=[CH:20]/[C:21](Cl)=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.[C:48]([OH:53])(=[O:52])[C:49]([OH:51])=[O:50]>C(OCC)(=O)C>[C:48]([OH:53])(=[O:52])[C:49]([OH:51])=[O:50].[CH3:17][CH:18]([CH3:24])/[CH:19]=[CH:20]/[C:21]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:6]2[CH:14]=[CH:15][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[N:16]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 10986269(E)-4-methylpent-2-enoyl ChlorideHCID 227366532-amino-4-methoxy-N-(2-pyridyl)aniline

Product 1

HCID 22736729(E)-2-(3-Methyl-1-butenyl)-5-methoxy-1-(2-pyridyl)-1H-benzimidazole oxalate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Free base of the titled compound was prepared from 4-methoxy-2-amino-N-(2-pyridyl)aniline and (E)-4-methyl-2-pentenoyl chloride according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base and oxalic acid were dissolved into ethyl acetate. Concentration and recrystallization from ethyl acetate/n-hexane yielded the titled compound.

Workup

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

Sources & evidence

ORD record
ord-17e2e97ba1dc461d9e850b4285f04593
Source dataset
uspto-grants-2001_10
Patent number
US06310079B1

Reaction notes

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