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

HRID 50884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50884
[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].[CH3:15][O:16][C:17]1[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=1[CH:19]=[CH:20][C:21](Cl)=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.[C:51]([OH:56])(=[O:55])[C:52]([OH:54])=[O:53]>C(OCC)(=O)C>[C:51]([OH:56])(=[O:55])[C:52]([OH:54])=[O:53].[CH3:15][O:16][C:17]1[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=1/[CH:19]=[CH:20]/[C:21]1[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]=1

Komponenten

6

Edukt 4

HCID 971Oxalic AcidHCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 534112862-Propenoyl chloride, 3-(2-methoxyphenyl)-, (E)-

Produkt 1

HCID 22736717(E)-2-Methoxystyryl-1-(2-pyridyl)-1H-benzimidazole oxalate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and 2-methoxycinnamoyl chloride (Vallaerda, J.; Appelberg, U.; Csoeregh, I.; Hacksell, U. J. Chem. Soc. Perkin Trans. I; 1994, 17, 461) 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: 417.42; mp: 123.0-125.0° C.; 1H-NMR (DMSO) δ: 8.81-8.77 (1H, m), 8.20 (1H, td, J=7.7,2.0 Hz), 8.10 (1H, d, J=16.1 Hz), 7.75 (2H, dd, J=8.1, 1.1 Hz), 7.68-7.62 (1H, m), 7.57 (1H, dd, J=7.7, 1.5 Hz), 7.46-7.42 (1H, m), 7.39-7.23 (4H, m) 7.08 (1H, d, J=7.7 Hz), 6.97 (1H, t, J=7.3 Hz), 3.86 (3H, s).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-70607436b43e4cd99edcdc69b4ae7ef6
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713482B2

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