Phosphorus oxychloride → 1-Phenyl-2-(3,4-dimethylphenyl)-6-methoxybenzimidazole

HRID 741758

Reaktionsgleichung

Reaktionsgleichung von HRID 741758
[CH3:1]C1C=C(C=CC=1C)C(Cl)=O.[C:12]1([N:18]2[C:22]3[CH:23]=[C:24]([OH:27])[CH:25]=[CH:26][C:21]=3[N:20]=[C:19]2[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([CH3:35])[CH:29]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.P(Cl)(Cl)(Cl)=O>[Pd].C1(NC2C=C(C=CC=2OC)N)C=CC=CC=1>[C:12]1([N:18]2[C:22]3[CH:23]=[C:24]([O:27][CH3:1])[CH:25]=[CH:26][C:21]=3[N:20]=[C:19]2[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([CH3:35])[CH:29]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 27585353,4-Dimethylbenzoyl chlorideHCID 193539421-Phenyl-2-(3,4-dimethylphenyl)-6-hydroxybenzimidazole

Produkt 1

HCID 193540191-Phenyl-2-(3,4-dimethylphenyl)-6-methoxybenzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 193539323-Phenylamino-4-methoxyanilineLösungsmittel

Versuchsvorschrift

The nitro group of the above-described intermediate was then reduce to an amino group by catalytic hydrogenation using a palladium on activated carbon catalyst, essentially as previously described, resulting in 3-phenylamino-4-methoxyaniline with was then reacted with 3,4-dimethylbenzoyl chloride as previously described. This intermediate was then cyclized to the corresponding benzimidazole with phosphorous oxychloride as previously described to yield 1-phenyl-2-(3,4-dimethylphenyl)-6-methoxybenzimidazole.

Quellen und Nachweise

ORD-Eintrag
ord-b49f94910c294cfb9cc8aad2b8a2eb8f
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05552426

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