Sodium hydride → 1-(4-Tert-butyldimethylsilyloxy-3-propylphenylmethyl)-3-carboethoxy-2-benzimidazolinone

HRID 274939Notes

Reaction equation

HRID 274939 reaction equation
[C:1]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15])([O:3][CH2:4][CH3:5])=[O:2].[H-].[Na+].[Si:18]([O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][C:27]=1[CH2:34][CH2:35][CH3:36])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[Si:18]([O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][N:8]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])[C:7]2=[O:15])=[CH:28][C:27]=1[CH2:34][CH2:35][CH3:36])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 303857Ethyl 2-oxo-2,3-dihydro-1H-benzo[D]imidazole-1-carboxylateHCID 200892104-Tert-butyldimethylsilyloxy-3-propylbenzyl bromide

Product 1

HCID 200891961-(4-Tert-butyldimethylsilyloxy-3-propylphenylmethyl)-3-carboethoxy-2-benzimidazolinoneYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 0.295 g (1.43 mmol) of 1-carboethoxy-2-benzimidazolinone dissolved in 5.0 mL DMF was added 0.063 g (1.57 mmol) of a 60% oil dispersion of sodium hydride and the resulting mixture was stirred under a nitrogen atmosphere and gently warmed with a heat gun until the solids had dissolved and gas evolution had ceased. A solution of the product of step A in 2.0 mL DMF was then added and the reaction mixture was stirred for an additional 0.5 hours. The mixture was then quenched with 10% aqueous citric acid and extracted into ethyl acetate. The organic layer was separated, washed with saturated sodium bicarbonate and brine, dried (MgSO4), filtered and evaporated, and then the residue was purified on a silica gel flash chromatography column eluted with 30% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded 0.088 g (64%) of the title compound.

Workup

  1. temperaturegently warmed with a heat gun until the solids
  2. dissolutionhad dissolved
  3. stirringthe reaction mixture was stirred for an additional 0.5 hours
  4. customThe mixture was then quenched with 10% aqueous citric acid
  5. extractionextracted into ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with saturated sodium bicarbonate and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customthe residue was purified on a silica gel flash chromatography column
  12. washeluted with 30% EtOAc-hexane
  13. customEvaporation of the purified fractions
  14. customdrying in vacuo

Sources & evidence

ORD record
ord-842cb5f8ca674bc9866193082f4058b7
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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