Oxalic Acid → (E)-5-Methoxy-1-(2-Pyridyl)-2-[2-(2-thienyl)ethenyl]-1H-benzimidazole oxalate

HRID 50949Notes

Reaction equation

HRID 50949 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.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1/[CH:22]=[CH:23]/[C:24](Cl)=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.[C:50]([OH:55])(=[O:54])[C:51]([OH:53])=[O:52]>C(OCC)(=O)C>[C:50]([OH:55])(=[O:54])[C:51]([OH:53])=[O:52].[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[C:24](/[CH:23]=[CH:22]/[C:18]3[S:17][CH:21]=[CH:20][CH:19]=3)=[N:16][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 112637803-(2-Thienyl)acryloyl chlorideHCID 227366532-amino-4-methoxy-N-(2-pyridyl)aniline

Product 1

HCID 22736685(E)-5-Methoxy-1-(2-Pyridyl)-2-[2-(2-thienyl)ethenyl]-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)-3-(2-thienyl)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. MW: 423.45; mp: 180.0-181.0° C.; 1H-NMR (DMSO) δ: 8.76 (1H, d, J=4.0 Hz), 8.18 (1H, td, J=7.3, 1.8 Hz), 7.99 (1H, d, J=15.8 Hz), 7.72 (1H, d, J=7.7 Hz), 7.65-7.56 (2H, m), 7.42 (1H, d, J=3.7 Hz), 7.34 (1H, d, J=8.8 Hz), 7.24 (1H, d, J=2.2 Hz), 7.14-7.09 (1H, m), 6.92-6.84 (2H, m), 3.83 (3H, s).

Workup

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

Sources & evidence

ORD record
ord-ace22e8a13be4e638eaccf2756dc293a
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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