Sodium hydride → Ethyl 3-[methoxycarbonyl-(2-methoxyphenyl)methyl]-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

HRID 1643949Notes

Reaction equation

HRID 1643949 reaction equation
[O:1]=[C:2]1[N:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[NH:3]1.[H-].[Na+].Br[CH:19]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31])[C:20]([O:22][CH3:23])=[O:21].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[CH3:23][O:22][C:20]([CH:19]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31])[N:3]1[C:4]2[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=2[N:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]1=[O:1])=[O:21]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 303857Ethyl 2-oxo-2,3-dihydro-1H-benzo[D]imidazole-1-carboxylateHCID 14234296Methyl 2-bromo-2-(2-methoxyphenyl)acetate

Product 1

HCID 24901090Ethyl 3-[methoxycarbonyl-(2-methoxyphenyl)methyl]-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2.61 g (12.7 mmol) of ethyl 2-oxo-2,3-dihydrobenzimidazole-1-carboxylate (IV) were dissolved in dry DMF (40 ml) in a heat-dried flask under a nitrogen atmosphere. 532 mg (13.3 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, 3.54 g (13.7 mmol) of methyl bromo-(2-methoxyphenyl)acetate 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 50% ethyl acetate in heptane). Yield: 3.21 g (66%) of colorless 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 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-febe08951a4e498090b3296aed905ef5
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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