1,3-Dichloro-5,5-dimethylhydantoin → HCID 71279168, compound

HRID 1621094Notes

Reaction equation

HRID 1621094 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:11]([O:13][CH3:14])=[O:12])[N:4]=[CH:3]1.[Cl:15]N1C(C)(C)C(=O)N(Cl)C1=O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.CCCCCCC>CN(C=O)C>[Cl:15][C:3]1[N:2]([CH3:1])[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:11]([O:13][CH3:14])=[O:12])[N:4]=1

Participants

6

Reactant 4

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 516892Sodium BicarbonateHCID 597451HCID 597451, compoundHCID 21899848Ethylacetate heptane

Product 1

HCID 71279168HCID 71279168, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a colorless solution of dimethyl 1-methyl-1H-imidazole-4,5-dicarboxylate (500 mg, 2.42 mmol, Eq: 1.00) in DMF (5.00 mL) was added under a nitrogen atmosphere 1,3-dichloro-5,5-dimethylhydantoin (487 mg, 2.42 mmol, Eq: 1.00). The reaction mixture was heated to 80° C. and stirred for 2 h, cooled down to ambient temperature, poured into saturated sodium bicarbonate solution (5 mL) and extracted with ethyl acetate (2×10 mL). The organic layers were washed with brine (5 mL), dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) to give the product as colorless oil (415 mg, 1.78 mmol, 73.7%). MS: M=233.0 (M+H)+

Workup

  1. temperaturecooled down to ambient temperature
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. washThe organic layers were washed with brine (5 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (

Sources & evidence

ORD record
ord-29888b93eb044d6bacafcd0d84443c64
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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