Isopropyl iodide → HCID 58550608, compound

HRID 1890703Notes

Reaction equation

HRID 1890703 reaction equation
[CH3:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].C(=O)([O-])[O-].[K+].[K+].I[CH:22]([CH3:24])[CH3:23]>CN(C=O)C>[CH:22]([N:4]1[C:3](=[O:8])[C:2]([CH3:1])([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:6][C:5]1=[O:7])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 930435-Methyl-5-phenylhydantoin

Product 1

HCID 58550608HCID 58550608, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (±)-5-methyl-5-phenylhydantoin (3.0 g, 15.7 mmol) in DMF (20 mL) was added potassium carbonate (2.6 g, 18.9 mmol) and 2-iodopropane (3.2 g, 18.9 mmol). The reaction was stirred at ambient temperature for 18 h and then partitioned between EtOAc (100 mL) and H2O (100 mL). The layers were separated and the aqueous phase was extracted further with EtOAc (2×100 mL). The combined organic extracts were washed with brine (100 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—75:25 to 50:50, to give the title compound. MS: m/z=233 (M+1).

Workup

  1. custompartitioned between EtOAc (100 mL) and H2O (100 mL)
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted further with EtOAc (2×100 mL)
  4. washThe combined organic extracts were washed with brine (100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-3153217da7b64baa9fdfa57a9fbf4cb2
Source dataset
uspto-grants-2013_08
Patent number
US08507477B2

Reaction notes

Loading…