1,3-Dibromo-5,5-dimethylhydantoin → HCID 15539190, compound

HRID 1900536Notes

Reaction equation

HRID 1900536 reaction equation
[C:1]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:14]N1C(C)(C)C(=O)N(Br)C1=O>C1(C)C=CC=CC=1>[Br:14][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8]

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 96345tert-Butyl ethyl malonate

Product 1

HCID 15539190HCID 15539190, compoundYield 176.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

t-Butyl ethyl malonate (25.00 g, 0.13 mol) was dissolved in toluene and warmed to 80° C. To the resulting solution was added 1,3-dibromo-5,5-dimethylhydantoin (25.00 g, 0.07 mol). The reaction was stirred at elevated (80° C.) temperature 18 hr. The reaction was cooled, concentrated and taken up in Et2O. The organic layer was washed with saturated NaHCO3 (2×), brine (3×), dried (MgSO4), filtered and concentrated. Purification by filtration on silica (70:30-heptane:ethyl acetate) yielded 33.0 g (93%) of a light yellow oil. NMR and MS indicated a mixture of three compounds, starting material (20%), monobrominated (55%) and dibromonated diesters (25%). The material was used without further purification.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. washThe organic layer was washed with saturated NaHCO3 (2×), brine (3×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification
  8. filtrationby filtration on silica (70:30-heptane:ethyl acetate)

Sources & evidence

ORD record
ord-dffa5d120bc74176a0c4e8a702b2f3ff
Source dataset
uspto-grants-1996_11
Patent number
US05576167

Reaction notes

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