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

HRID 382538Notes

Reaction equation

HRID 382538 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.

Workup

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

Sources & evidence

ORD record
ord-f345976609fd436caf51f8d8478d0ff0
Source dataset
uspto-grants-2001_10
Patent number
US06310079B1

Reaction notes

Loading…