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

HRID 274941Notes

Reaction equation

HRID 274941 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:10]2=[O:23])=[CH:4][C:3]=1[CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:34]([C:40]1[CH:45]=[CH:44][C:43]2[O:46][CH2:47][O:48][C:42]=2[CH:41]=1)[C:35]([O:37][CH2:38][CH3:39])=[O:36]>CN(C=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:35]([CH:34]([C:40]1[CH:45]=[CH:44][C:43]2[O:46][CH2:47][O:48][C:42]=2[CH:41]=1)[O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:10]2=[O:23])=[CH:4][C:3]=1[CH2:24][CH2:25][CH3:26])([O:37][CH2:38][CH3:39])=[O:36]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 15383768Ethyl alpha-bromo-3,4-methylenedioxyphenylacetateHCID 200891871-(4-Hydroxy-3-propylphenylmethyl)-3-carboethoxy-2-benzimidazolinone

Product 1

HCID 200891921-[4-(1-Carboethoxy-1-(3,4-methylenedioxyphenyl)methoxy)-3-propylphenylmethyl]-3-carboethoxy-2-benzimidazolinoneYield 83%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 0.105 g (0.30 mmol) of the product of step C in 1.0 mL of DMF was added 0.115 g (0.33 mmol) of cesium carbonate and the resulting suspension was stirred under a nitrogen atmosphere for 15 minutes. A solution of 0.094 g (0.33 mmol) ethyl α-bromo-3,4-methylenedioxyphenylacetate in 0.5 mL of DMF was then added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then suspended in 10% aqueous citric acid and extracted into ethyl acetate. The organic layer was separated, washed with saturated sodium bicarbonate, brine, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 30% EtOAc-hexane; combination of the product fractions and evaporation in vacuo afforded 0.137 g (83%) of the title compound.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. extractionextracted into ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with saturated sodium bicarbonate, 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. customcombination of the product fractions and evaporation in vacuo

Sources & evidence

ORD record
ord-15778c484e1741f39a1e7ba002b98059
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

Loading…