Water → 1-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-one

HRID 274929Notes

Reaction equation

HRID 274929 reaction equation
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8]1=O.CI.O>CN(C=O)C>[CH3:8][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:1]1=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 119852-Hydroxy benzimidazole

Product 1

HCID 5905401-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-oneYield 12%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (814.5 mg, 2.5 mmol) was added to a stirred solution of benzimidazolinone (335 mg, 2.5 mmol) in DMF (10 mL) under nitrogen at room temperature. After stirring for 30 min., methyl iodide (355 mg, 2.5 mmol) was added and the mixture stirred at room temperature for 18 h. Water was added and the mixture extracted with ethyl acetate. The organic phase was washed with water, dried (magnesium sulfate) and the solvent removed in vacuo. The residue was chromatographed (10-50% ethyl acetate/hexane) to give the title compound (43 mg, 12%) as a white solid.

Workup

  1. stirringthe mixture stirred at room temperature for 18 h
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried (magnesium sulfate)
  5. customthe solvent removed in vacuo
  6. customThe residue was chromatographed (10-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e58abdb7fe3240ff8a5206f8272ce9ec
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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