Oxalic Acid → HCID 22736776, compound

HRID 50898Notes

Reaction equation

HRID 50898 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].[CH2:15]([O:17][C:18]1[CH:28]=[CH:27][C:21]([CH:22]=[CH:23][C:24](Cl)=O)=[CH:20][CH:19]=1)[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].[O:17]([C:18]1[CH:28]=[CH:27][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:20][CH:19]=1)[CH2:15][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 53411295HCID 53411295, compound

Product 1

HCID 22736776HCID 22736776, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and 4-ethoxycinnamoyl chloride (Lohar, J. M.; Mahsru, U. Indian J. Chem. Sect. A, 1981, 20, 125) 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: 431.45; mp: 169.0-170.0° C.; 1H-NMR (DMSO) δ: 8.78 (1H, dd, J=5.1, 1.4 Hz), 8.18 (1H, td, J=7.7, 1.8 Hz), 7.85 (1H, d, J=16.1 Hz), 7.73 (2H, t, J=6.8 Hz), 7.67-7.61 (1H, m), 7.55 (2H, d, J=8.8 Hz), 7.43 (1H, d, J=7.7 Hz), 7.35-7.22 (2H, m), 7.01 (1H, d, J=16.1 Hz), 6.94 (2H, d, J=8.8 Hz), 4.06 (2H, q, J=7.0 Hz), 1.33 (3H, t, J=7.0 Hz).

Workup

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

Sources & evidence

ORD record
ord-4c7a7836598248f18677fcc5a8a9fbaa
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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