Oxalic Acid → (E)-1-(2-Pyrimidyl)-2-styryl-1H-benzimidazole oxalate

HRID 50877

Reaction equation

HRID 50877 reaction equation
[CH:1]([C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:19]1[N:24]=[CH:23][CH:22]=[CH:21][N:20]=1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.[C:48]([OH:53])(=[O:52])[C:49]([OH:51])=[O:50]>C(OCC)(=O)C>[C:48]([OH:53])(=[O:52])[C:49]([OH:51])=[O:50].[N:20]1[CH:21]=[CH:22][CH:23]=[N:24][C:19]=1[N:13]1[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=[C:9]1/[CH:1]=[CH:2]/[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 744042-ChloropyrimidineHCID 2429652-(2-Phenylethenyl)-1h-benzimidazoleHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole

Product 1

HCID 9930183(E)-1-(2-Pyrimidyl)-2-styryl-1H-benzimidazole oxalate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Free base of the titled compound was prepared from 2-styryl-1H-benzimidazole and 2-Chloropyrimidine according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method B). The free base and oxalic acid were dissolved into ethyl acetate. Concentration and recrystallization from ethyl acetate-hexane yielded the titled compound. MW: 388.39; mp: 167.0-168.0° C.; 1H-NMR (DMSO-d6) δ: 9.09 (2H, dd, J=5.1, 0.7), 8.13-8.07 (1H, m), 7.91 (2H, s), 7.76-7.70 (2H, m), 7.76 (1H, d, J=7.3 Hz), 7.63 (1H, td, J=4.8, 0.7 Hz), 7.41 (1H, d, J=7.7 Hz), 7.46-7.30 (4H, m).

Workup

  1. concentrationConcentration and recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-65a993428f174614bc116aa383312db5
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Linked notes

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