Oxalic Acid → (E)-6-Methoxy-1-(2-pyridyl)-2-styryl-1H-benzimidazole oxalate

HRID 50937Notes

Reaction equation

HRID 50937 reaction equation
[CH3:1][O:2]C1C=CC([N+]([O-])=O)=C(C=1)N.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]1[C:23]2[CH:24]=[CH:25][C:26](C(F)(F)F)=[CH:27][C:22]=2[N:21]=[C:20]1/[CH:32]=[CH:33]/[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[C:40]([OH:45])(=[O:44])[C:41]([OH:43])=[O:42]>C(OCC)(=O)C>[C:40]([OH:45])(=[O:44])[C:41]([OH:43])=[O:42].[CH3:1][O:2][C:25]1[CH:26]=[CH:27][C:22]2[N:21]=[C:20](/[CH:32]=[CH:33]/[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:19]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=3)[C:23]=2[CH:24]=1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 853005-Methoxy-2-nitroanilineHCID 22736704(E)-1-(2-pyridyl)-2-styryl-5-trifluoromethyl-1H-benzimidazole

Product 1

HCID 22736778(E)-6-Methoxy-1-(2-pyridyl)-2-styryl-1H-benzimidazole oxalate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Free base of the titled compound was prepared from 5-methoxy-2-nitroaniline according to the preparation of (E)-1-(2-pyridyl)-2-styryl-5-trifluoromethyl-1H-benzimidazole (Example 57). The free base and oxalic acid were dissolved into ethyl acetate. Concentration and recrystallization from ethyl acetate-hexane yielded the titled compound. MW: 417.42; mp: 172.0-174.0° C.; 1H-NMR (DMSO) δ: 8.78-8.76 (1H, m), 8.18 (1H, td, J=7.8, 2.1 Hz), 7.78 (1H, d, J=16.1 Hz), 7.74 (1H, d, J=8.1 Hz), 7.66-7.55 (4H, m), 7.41-7.32 (3H, m), 7.11 (1H, d, J=15.8 Hz), 6.98-6.91 (2H, m), 3.75 (3H, s).

Workup

  1. concentrationConcentration and recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-acec41c588c344819ea2dcfd758ac8c7
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

Loading…