Acetic Acid → 2-(2,3-Dihydro-2-oxo-1H-benzo[d]imidazol-5-yl)propanoic acid

HRID 1626842Notes

Reaction equation

HRID 1626842 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]([CH3:17])[C:12]([O:14]CC)=[O:13])=[CH:10][C:4]=2[NH:3]1.CCO.[OH-].[Na+].CC(O)=O>O>[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]([CH3:17])[C:12]([OH:14])=[O:13])=[CH:10][C:4]=2[NH:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 44543173Ethyl 2-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-5-yl)propanoate

Product 1

HCID 155580362-(2,3-Dihydro-2-oxo-1H-benzo[d]imidazol-5-yl)propanoic acidYield 63.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To the flask of Ethyl 2-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-5-yl)propanoate (175 mg, 0.747 mmol) was added 90% aq. EtOH (5 mL) at room temperature, and additionally added NaOH (70 mg). The reaction mixture was stirred for 10 hrs at 40° C. then cooled to room temperature. The mixture was diluted with H2O (25 mL) and acidified with AcOH (4 mL, pH=4) then extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using CH2Cl2:MeOH (10:1) as eluant. Pale brown solid, yield: 63.6%

Workup

  1. temperaturethen cooled to room temperature
  2. extractionthen extracted with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-c298171a605145c5ba73ed2227a71b17
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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