Cesium carbonate → 1-[4-(1-Carbomethoxy-1-(3,4-methylenedioxyphenyl)methoxy)-3-chloro-5-propylphenylmethyl]-3-carboethoxy-2-benzimidazolinone

HRID 274934Notes

Reaction equation

HRID 274934 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:44]=[C:43]([CH2:45][CH2:46][CH3:47])[C:27]([O:28][CH:29]([C:34]2[CH:39]=[CH:38][C:37]3[O:40][CH2:41][O:42][C:36]=3[CH:35]=2)[C:30]([O:32][CH3:33])=[O:31])=[C:26]([Cl:48])[CH:25]=1>CN(C=O)C>[C:30]([CH:29]([C:34]1[CH:39]=[CH:38][C:37]2[O:40][CH2:41][O:42][C:36]=2[CH:35]=1)[O:28][C:27]1[C:43]([CH2:45][CH2:46][CH3:47])=[CH:44][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:25][C:26]=1[Cl:48])([O:32][CH3:33])=[O:31]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 303857Ethyl 2-oxo-2,3-dihydro-1H-benzo[D]imidazole-1-carboxylateHCID 20089193Methyl 2-(4-bromomethyl-2-chloro-6-propylphenoxy)-2-(3,4-methylenedioxyphenyl)acetate

Product 1

HCID 200891971-[4-(1-Carbomethoxy-1-(3,4-methylenedioxyphenyl)methoxy)-3-chloro-5-propylphenylmethyl]-3-carboethoxy-2-benzimidazolinoneYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 0.069 g (0.33 mmol) of 1-carboethoxy-2-benzimidazolinone dissolved in 0.6 mL DMF was added 0.217 g (0.66 mmol) of powdered cesium carbonate and the resulting suspension was stirred under a nitrogen atmosphere at room temperature for 30 minutes. A solution of the product of step E in 0.5 mL DMF was then added and the reaction mixture was stirred for an additional 15 hours. The mixture was then partitioned between EtOAc and water and extracted. 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 (45%) of the title compound.

Workup

  1. stirringthe reaction mixture was stirred for an additional 15 hours
  2. customThe mixture was then partitioned between EtOAc and water
  3. extractionextracted
  4. customThe organic layer was separated
  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-1b8a1fca666640f7accdecd07afc47b0
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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