Dimethylhydantoin → HCID 14678127, compound

HRID 1597424Notes

Reaction equation

HRID 1597424 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CN(C=O)C>[CH3:1][C:2]1([CH3:9])[C:3](=[O:8])[N:4]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5](=[O:7])[NH:6]1

Participants

5

Reactant 3

HCID 6491DimethylhydantoinHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonate

Product 1

HCID 14678127HCID 14678127, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5,5-dimethylhydantoin (10 g, 78 mmol) in DMF (400 mL) was treated with cesium carbonate (25 g, 78 mmol) stirred at r.t. for 30 min then treated with ethyl bromoacetate (11.3 mL, 102 mmol) and allowed to stir overnight. The reaction mixture was partitioned between ethyl acetate and a 1 to 1 mixture of brine and water. The organics were washed with brine, dried (Na2SO4), filtered, concentrated and purified via silica gel column chromatography eluting with 30 to 50% ethyl acetate/hexane to give 5.47 g of the title compound as a white solid.

Workup

  1. stirringto stir overnight
  2. customThe reaction mixture was partitioned between ethyl acetate
  3. additiona 1 to 1 mixture of brine and water
  4. washThe organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified via silica gel column chromatography
  9. washeluting with 30 to 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2c369d45b11e488d9c15e9d63e640147
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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