Cesium carbonate → 1-[4-(1-Carboethoxy-1-(3,4-methylenedioxyphenyl)methoxy)phenylmethyl]-3-carboethoxy-2-benzimidazolinone

HRID 274945Notes

Reaction equation

HRID 274945 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].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:23][C:24]1[CH:45]=[CH:44][C:27]([O:28][CH:29]([C:35]2[CH:40]=[CH:39][C:38]3[O:41][CH2:42][O:43][C:37]=3[CH:36]=2)[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][CH:25]=1>CN(C=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:30]([CH:29]([C:35]1[CH:40]=[CH:39][C:38]2[O:41][CH2:42][O:43][C:37]=2[CH:36]=1)[O:28][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][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:45][CH:44]=1)([O:32][CH2:33][CH3:34])=[O:31]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 303857Ethyl 2-oxo-2,3-dihydro-1H-benzo[D]imidazole-1-carboxylateHCID 20089188Ethyl 2-(4-bromomethylphenoxy)-2-(3,4-methylenedioxyphenyl)acetate

Product 1

HCID 200891941-[4-(1-Carboethoxy-1-(3,4-methylenedioxyphenyl)methoxy)phenylmethyl]-3-carboethoxy-2-benzimidazolinoneYield 58%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 0.020 g (0.10 mmol) of 1-carboethoxy-2-benzimidazolinone dissolved in 250 gL DMF was added 0.035 g (0.11 mmol) of cesium carbonate and the resulting suspension was stirred under a nitrogen atmosphere for 10 minutes. A solution of the product of step B in 300 aL DMF was then added and the reaction mixture was stirred for an additional 1 hour. The mixture was suspended in 10% aqueous citric acid and extracted into ethyl acetate. The organic layer was separated, washed with saturated sodium bicarbonate and brine, dried (MgSO4), filtered, 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 0.029 g (58%) of the title compound.

Workup

  1. stirringthe reaction mixture was stirred for an additional 1 hour
  2. extractionextracted into ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with saturated sodium bicarbonate and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customthe residue was purified on a silica gel flash chromatography column
  9. washeluted with 30% EtOAc-hexane
  10. customEvaporation of the purified fractions
  11. customdrying in vacuo

Sources & evidence

ORD record
ord-6f40a9f8295343e9b5e63dd438934b4b
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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