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

HRID 1258455Notes

Reaction equation

HRID 1258455 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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%).

Workup

  1. filtrationThe formed precipitate was collected by filtration

Sources & evidence

ORD record
ord-98907de34e5d46ce86a21a1837a45810
Source dataset
uspto-grants-2013_06
Patent number
US08466166B2

Reaction notes

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