Oxalic Acid → (E)-4-Isopropylstyryl-1-(2-pyridyl)-1H-benzimidazole oxalate

HRID 50895Notes

Reaction equation

HRID 50895 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].[CH:15]([C:18]1[CH:28]=[CH:27][C:21]([CH:22]=[CH:23][C:24](Cl)=O)=[CH:20][CH:19]=1)([CH3:17])[CH3:16].N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.[C:52]([OH:57])(=[O:56])[C:53]([OH:55])=[O:54]>C(OCC)(=O)C>[C:52]([OH:57])(=[O:56])[C:53]([OH:55])=[O:54].[CH:15]([C:18]1[CH:19]=[CH:20][C:21](/[CH:22]=[CH:23]/[C:24]2[N:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=2)=[CH:27][CH:28]=1)([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 53411297HCID 53411297, compound

Product 1

HCID 69912132(E)-4-Isopropylstyryl-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 4-isopropylcinnamoyl chloride (Perkin, W. H. J. Chem. Soc., 1877, 31, 388) 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: 429.48; mp: 136.0-137.0° C.; 1H-NMR (DMSO) δ: 8.80-8.77 (1H, m), 8.19 (1H, td, J=7.9, 1.8 Hz), 7.86 (1H, d, J=16.1 Hz), 7.77-7.72 (2H, m), 7.67-7.61 (1H, m), 7.53 (2H, d, J=8.1 Hz), 7.47-7.43 (1H, m), 7.36-7.24 (2H, m), 7.27 (2H, d, J=8.4 Hz), 7.12 (1H, d, J=16.1 Hz), 2.52-2.49 (1H, m), 1.20 (6H, d, J=6.6 Hz).

Workup

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

Sources & evidence

ORD record
ord-4631588579d5433d8466122b68f830dc
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

Loading…