Water → (2-Butyl-benzoimidazol-1-yl)-acetic acid

HRID 487196Notes

Reaction equation

HRID 487196 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]([O:24]CC)=[O:23].O>CN(C)C=O>[CH2:1]([C:5]1[N:6]([CH2:21][C:22]([OH:24])=[O:23])[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 22122Benzimidazole, 2-butyl-

Product 1

HCID 2772534(2-Butyl-benzoimidazol-1-yl)-acetic acidYield 56.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-n-Butyl benzimidazole (3.00 g, 17.22 mmol) was mixed with powdered potassium carbonate (2.62 g, 19 mmol) and diluted with 25 mL dimethylformamide. To this was added ethyl bromoacetate (18.94 mmol). The reaction mixture was stirred at ambient temperature overnight and poured into 150 mL of water. The resulting crystals were filtered, and recrystallized from hexane to give 2.26 g (50%) of a solid; mp 70°-71° C.

Workup

  1. filtrationThe resulting crystals were filtered
  2. customrecrystallized from hexane

Sources & evidence

ORD record
ord-50a4c211eaaa4601907bd9db0fd8691c
Source dataset
uspto-grants-1994_03
Patent number
US05294631

Reaction notes

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