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Oxalic Acid → (E)-5-Ethoxy1-1-(2-pyridyl)-2-styryl-1H-benzimidazole oxalate

HRID 50929
Notes
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Reaction equation

HRID 50929 reaction equation
[CH2:1]([O:3]C1C=CC(N)=C([N+]([O-])=O)C=1)[CH3:2].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[C:24]2[CH:25]=[CH:26][C:27](C(F)(F)F)=[CH:28][C:23]=2[N:22]=[C:21]1/[CH:33]=[CH:34]/[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[C:41]([OH:46])(=[O:45])[C:42]([OH:44])=[O:43]>C(OCC)(=O)C>[C:41]([OH:46])(=[O:45])[C:42]([OH:44])=[O:43].[O:3]([C:27]1[CH:26]=[CH:25][C:24]2[N:20]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=3)[C:21](/[CH:33]=[CH:34]/[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[N:22][C:23]=2[CH:28]=1)[CH2:1][CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 692294-Ethoxy-2-nitroanilineHCID 22736704(E)-1-(2-pyridyl)-2-styryl-5-trifluoromethyl-1H-benzimidazole

Product 1

HCID 22736673(E)-5-Ethoxy1-1-(2-pyridyl)-2-styryl-1H-benzimidazole oxalate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Free base of the titled compound was prepared from 4-ethoxy-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/n-hexane yielded the titled compound. MW: 435.05; mp: 215.5-216.0° C.; 1H-NMR (DMSO-d6) δ: 8.78-8.75 (1H. m), 8.17 (1H, td, J=7.7, 1.8 Hz), 7.85 (1H, d, J=15.8 Hz), 7.72 (1H, d, J=8.1 Hz), 7.65-7.59 (3H, m), 7.44-7.33 (4H, m), 7.24 (1H, d, J=2.6 Hz), 7.18 (1H, d, J=15.8 Hz), 6.89 (1H, dd, J=8.8, 2.2 Hz), 4.10 (2H, q, J=7.0 Hz), 1.37 (3H, t, J=7.0 Hz).

Workup

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

Sources & evidence

ORD record
ord-12d3b2bf34fe4d54b86a1eee389a894e
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06713482B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes