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

HRID 50940Notes

Reaction equation

HRID 50940 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.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1/[CH:21]=[CH:22]/[C:23](Cl)=O.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].[CH3:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=3)[C:23](/[CH:22]=[CH:21]/[C:17]3[S:16][CH:20]=[CH:19][CH:18]=3)=[N:15][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 112637803-(2-Thienyl)acryloyl chlorideHCID 227367644-methyl-2-amino-N-(2-pyridyl)aniline

Product 1

HCID 9909329(E)-5-Methyl-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-methyl-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: 417.42; mp: 181.5-182.0° C.; 1H-NMR (DMSO) δ: 8.78-8.72 (1H, m), 8.16 (1H, t, J=7.7 Hz), 8.00 (1H, d, J=15.8 Hz), 7.69 (1H, d, J=8.1 Hz), 7.62-7.50 (3H, m), 7.39 (1H, br.s), 7.31 (1H, d, J=8.1 Hz), 7.15-7.05 (2H, m), 6.86 (1H, d, J=15.8 Hz), 2.42 (3H, s).

Workup

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

Sources & evidence

ORD record
ord-be67d0d47be0462fbd3198216a25aed2
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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