Oxalic Acid → (E)-2-Methoxystyryl-1-(2-pyridyl)-1H-benzimidazole oxalate

HRID 382528Notes

Reaction equation

HRID 382528 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14].[CH3:15][O:16][C:17]1[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=1[CH:19]=[CH:20][C:21](Cl)=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.[C:51]([OH:56])(=[O:55])[C:52]([OH:54])=[O:53]>C(OCC)(=O)C>[C:51]([OH:56])(=[O:55])[C:52]([OH:54])=[O:53].[CH3:15][O:16][C:17]1[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=1/[CH:19]=[CH:20]/[C:21]1[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 534112862-Propenoyl chloride, 3-(2-methoxyphenyl)-, (E)-

Product 1

HCID 22736717(E)-2-Methoxystyryl-1-(2-pyridyl)-1H-benzimidazole oxalate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and 2-methoxycinnamoyl chloride (Vallaerda, J.; Appelberg, U.; Csoeregh, I.; Hacksell, U. J. Chem. Soc. Perkin Trans.I; 1994, 17, 461) 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-7a08d2ab6a0548f782cc56a43dfb05d4
Source dataset
uspto-grants-2001_10
Patent number
US06310079B1

Reaction notes

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