Oxalic Acid → (E)-1-(2-Pyridyl)-2-[2-(4-pyridyl)ethenyl]-1H-benzimidazole oxalate

HRID 50952

Reaktionsgleichung

Reaktionsgleichung von HRID 50952
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[N:3]=1.[N:17]1[CH:22]=[CH:21][C:20]([CH:23]=O)=[CH:19][CH:18]=1.Cl.Cl.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CN=1.[C:50]([OH:55])(=[O:54])[C:51]([OH:53])=[O:52]>CO>[C:50]([OH:55])(=[O:54])[C:51]([OH:53])=[O:52].[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[N:6]1[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[N:3]=[C:2]1/[CH:1]=[CH:23]/[C:20]1[CH:21]=[CH:22][N:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 971Oxalic AcidHCID 133894-PyridinecarboxaldehydeHCID 227366432-Methyl-1-(pyridin-2-yl)-1H-benzimidazoleHCID 22736657(E)-1-(2-Pyridyl)-2-[2-(2-pyridyl)ethenyl]-1H-benzimidazole dihydrochloride

Produkt 1

HCID 22736688(E)-1-(2-Pyridyl)-2-[2-(4-pyridyl)ethenyl]-1H-benzimidazole oxalate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Free base of the titled compound was prepared from 2-methyl-1-(2-pyridyl)-1H-benzimidazole and pyridine4-carboxaldehyde according to the preparation of (E)-1-(2-pyridyl)-2-[2-(2-pyridyl)ethenyl]-1H-benzimidazole dihydrochloride Example 44). The free base and oxalic acid were dissolved into MeOH. Concentration and recrystalization from ethyl MeOH/Et2O/n-hexane yielded the titled compound. MW: 388.39; mp: 203.6-205.3° C. (decomposed); 1H-NMR (DMSO) δ: 8.81-8.75 (1H, m), 8.62-8.55 (2H, m), 8.20 (1H, dt, J=1.9,7.7 Hz), 7.88 (1H, d, J=16.0 Hz), 7.81-7.74 (2H, m), 7.69-7.60 (3H, m), 7.52-7.46 (1H, m), 7.47 (1H, d, J=16.0 Hz) 7.40-7.28 (2H, m).

Aufarbeitung

  1. concentrationConcentration and recrystalization from ethyl MeOH/Et2O/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-e3440b1ca2a5458fa63bdfa72706bbc7
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713482B2

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