Oxalic Acid → (E)-2-[2-(3-Furyl)ethenyl]-5-methyl-1-(2-pyridyl)-1H-benzimidazole oxalate

HRID 382574Notes

Reaction equation

HRID 382574 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[C:4]([NH2:15])[CH:3]=1.[O:16]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23](Cl)=O)=[CH:17]1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.[C:49]([OH:54])(=[O:53])[C:50]([OH:52])=[O:51]>C(OCC)(=O)C>[C:49]([OH:54])(=[O:53])[C:50]([OH:52])=[O:51].[O:16]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=3)[C:5]3[CH:13]=[CH:14][C:2]([CH3:1])=[CH:3][C:4]=3[N:15]=2)=[CH:17]1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 22736687(E)-3-(Furan-3-yl)acryloyl chlorideHCID 227367644-methyl-2-amino-N-(2-pyridyl)aniline

Product 1

HCID 9800620(E)-2-[2-(3-Furyl)ethenyl]-5-methyl-1-(2-pyridyl)-1H-benzimidazole oxalate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Free base of the titled compound was prepared from 4-methyl-2-amino-N-(2-pyridyl)aniline and (E)-3-(3-furyl)acryloyl 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-be50be5f31c547ed979ad09bb74c2756
Source dataset
uspto-grants-2001_10
Patent number
US06310079B1

Reaction notes

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