Ethylene Glycol → 7-(Benzyloxy)-1-(2-methoxyethyl)-2-methyl-1H-benzimidazole-5-carboxylic acid

HRID 1258455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258455
[CH2:1]([O:8][C:9]1[C:14]2[N:15]([CH2:19][CH2:20][O:21][CH3:22])[C:16]([CH3:18])=[N:17][C:13]=2[CH:12]=C(C#N)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:25].[K+].Cl.[CH2:28]([OH:31])[CH2:29]O>>[CH2:1]([O:8][C:9]1[C:14]2[N:15]([CH2:19][CH2:20][O:21][CH3:22])[C:16]([CH3:18])=[N:17][C:13]=2[CH:12]=[C:29]([C:28]([OH:31])=[O:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 672198857-(Benzyloxy)-1-(2-methoxyethyl)-2-methyl-1H-benzimidazole-5-carbonitrile

Produkt 1

HCID 672204647-(Benzyloxy)-1-(2-methoxyethyl)-2-methyl-1H-benzimidazole-5-carboxylic acidAusbeute 91 %

Versuchsvorschrift

A solution of 7-(benzyloxy)-1-(2-methoxyethyl)-2-methyl-1H-benzimidazole-5-carbonitrile (549 mg, 1.71 mmol, Step 4) and potassium hydroxide (85%, 564 mg, 8.54 mmol) in ethylene glycol (10 mL) was stirred at 135° C. for 5 hours. After cooling to room temperature, 2 mol/L hydrochloric acid was added until pH of the solution became about 3. The formed precipitate was collected by filtration to afford the title compound as a gray solid (530 mg, 91%).

Aufarbeitung

  1. filtrationThe formed precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-98907de34e5d46ce86a21a1837a45810
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466166B2

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