Sodium hydride → HCID 20089200, compound

HRID 274936Notes

Reaction equation

HRID 274936 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+].Br[CH2:19][C:20]1[CH:41]=[C:40]([Cl:42])[C:23]([O:24][CH:25]([C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:22]([Cl:43])[CH:21]=1>CN(C=O)C>[C:26]([CH:25]([C:31]1[CH:36]=[CH:35][C:34]2[O:37][CH2:38][O:39][C:33]=2[CH:32]=1)[O:24][C:23]1[C:40]([Cl:42])=[CH:41][C:20]([CH2:19][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:21][C:22]=1[Cl:43])([O:28][CH2:29][CH3:30])=[O:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 303857Ethyl 2-oxo-2,3-dihydro-1H-benzo[D]imidazole-1-carboxylateHCID 20089189Ethyl 2-(4-bromomethyl-2,6-dichlorophenoxy)-2-(3,4-methylenedioxyphenyl)acetate

Product 1

HCID 20089200HCID 20089200, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 0.048 g (0.24 mmol) of 1-carboethoxy-2-benzimidazolinone dissolved in 0.5 mL DMF was added 0.010 g (0.26 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. A solution of the product of step B in 1.0 mL DMF was then added and the reaction mixture was stirred for an additional 1.5 hours. The mixture was then quenched with 5% aqueous ammonium chloride and extracted into ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and evaporated, and 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 1.5 hours
  4. customThe mixture was then quenched with 5% aqueous ammonium chloride
  5. extractionextracted into ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customthe residue was purified on a silica gel flash chromatography column
  11. washeluted with 30% EtOAc-hexane
  12. customEvaporation of the purified fractions
  13. customdrying in vacuo

Sources & evidence

ORD record
ord-fbb5e74d72934b4f8e52a029c3d776fc
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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