Oxalic Acid → (E)-1-(2-Pyridyl)-2-styryl-5-methoxy-1H-benzimidazole oxalate

HRID 50928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50928
[CH3:1][O:2]C1C=CC(N)=C([N+]([O-])=O)C=1.[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].[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]([O:2][CH3:1])=[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

Komponenten

5

Edukt 3

HCID 971Oxalic AcidHCID 667934-Methoxy-2-nitroanilineHCID 22736704(E)-1-(2-pyridyl)-2-styryl-5-trifluoromethyl-1H-benzimidazole

Produkt 1

HCID 22736663(E)-1-(2-Pyridyl)-2-styryl-5-methoxy-1H-benzimidazole oxalate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Free base of the titled compound was prepared from 4-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/n-hexane yielded the titled compound. MW: 417.42; mp: 187.0-188.0° C.; 1H-NMR (DMSO-d6) δ: 8.76 (1H, dd, J=5.0, 1.3 Hz), 8.17 (1H, td, J=7.8,2.0 Hz), 7.85 (1H, d, J=15.8 Hz), 7.72 (1H, d, J=8.1 Hz), 7.65-7.58 (3H, m), 7.42-7.30 (4H, m), 7.26 (1H, d, J=2.2 Hz), 7.17 (1H, d, J=16.1 Hz), 6.90 (1H, dd, J=8.8, 2.6 Hz), 3.83 (3H, s).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-3ad2815c978041cfa15e99b2223ef6cd
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713482B2

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