Sodium hydride → HCID 66755623, compound

HRID 1643935Notes

Reaction equation

HRID 1643935 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[H-].[Na+].Br[CH:22]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[C:26]([O:25][C:23]([CH:22]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[N:8]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:18]=[CH:17][C:5]=2[N:6]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[C:7]1=[O:9])=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10468275tert-Butyl 5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylateHCID 11000147Tert-butyl 2-bromo-2-phenylacetate

Product 1

HCID 66755623HCID 66755623, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

4.00 g (14.9 mmol) of tert-butyl 5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate (Via) were dissolved in dry DMF (60 ml) in a heat-dried flask under a nitrogen atmosphere. 625 mg (15.6 mmol) of sodium hydride (60% suspension in mineral oil) were added while stirring at 0° C., and the reaction solution was then stirred at room temperature for 30 min. After renewed cooling in an ice bath, 4.44 g (16.4 mmol) of tert-butyl bromo-phenylacetate were added, and the mixture was stirred while cooling in ice for 1 h and then at room temperature for 2 h. The reaction solution was diluted with ethyl acetate, mixed with 10% aqueous ammonium chloride solution and then extracted with ethyl acetate (3×). The combined organic phases were washed with water and saturated NaCl solution, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (mobile phase gradient 15-35% ethyl acetate in cyclohexane). Yield: 6.91 g (100%) of yellow oil

Workup

  1. stirringthe reaction solution was then stirred at room temperature for 30 min
  2. temperatureAfter renewed cooling in an ice bath
  3. stirringthe mixture was stirred
  4. temperaturewhile cooling in ice for 1 h
  5. extractionextracted with ethyl acetate (3×)
  6. washThe combined organic phases were washed with water and saturated NaCl solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel (mobile phase gradient 15-35% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-8ab58c8fa74f463d90150dc7acb9a389
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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