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

HRID 50946Notes

Reaction equation

HRID 50946 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.[O:17]1[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24](Cl)=O)=[CH:18]1.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].[O:17]1[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[C:6]3[CH:14]=[CH:15][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[N:16]=2)=[CH:18]1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 227366532-amino-4-methoxy-N-(2-pyridyl)anilineHCID 22736687(E)-3-(Furan-3-yl)acryloyl chloride

Product 1

HCID 9866081(E)-2-[2-(3-Furyl)ethenyl]-1-(2-pyridyl)-5-methoxy-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-(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-hexane yielded the titled compound. MW: 407.39; mp: 196.0-198.0° C.; 1H-NMR (DMSO) δ: 8.75-8.73 (1H, m), 8.16 (1H, td, J=7.7, 1.8 Hz), 8.04 (1H, br.s), 7.76-7.58 (4H, m), 7.33 (1H, d, J=8.8 Hz), 7.23 (1H, d, J=2.2 Hz), 6.90-6.80 (3H, m), 3.82 (3H, s).

Workup

  1. concentrationConcentration and recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-01b2e0638ff24cf7952730d2361f956c
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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