1,3-Dibromo-5,5-dimethylhydantoin → HCID 67175327, compound

HRID 1791886Notes

Reaction equation

HRID 1791886 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12](=[O:15])[CH2:13][CH3:14].[Br:17]N1C(C)(C)C(=O)N(Br)C1=O>C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([CH2:10][Br:17])[CH:7]=[CH:6][C:5]=1[NH:11][C:12](=[O:15])[CH2:13][CH3:14]

Participants

6

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 43623650HCID 43623650, compound

Product 1

HCID 67175327HCID 67175327, compoundYield 106.6%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

The radical bromination was performed as described by Patil et al. 1989: 5-Methyl-2-propionylamino-benzoic acid methyl ester (8.85 g, 40 mmol) and 1,3-dibromo-5,5-dimethyl hydantoin (DDH) (5,72 g, 20 mmol) in a mixture of CHCl3 (500 mL) and CCl4 (500 mL) was heated to reflux. Every 60 minutes 50 mg of dibenzoyl peroxide was added for six hours and then the reaction mixture was left at reflux over night. It was then allowed to reach room temperature and the solvents were removed by evaporation. Chromatography using silica gel 60 and heptane/ethyl acetate (18:2 ->17:3 ->16:4) as eluent afforded the pure title compound (6.40 g, 53%).

Workup

  1. temperaturewas heated to reflux
  2. waitthe reaction mixture was left
  3. temperatureat reflux over night
  4. customto reach room temperature
  5. customthe solvents were removed by evaporation

Sources & evidence

ORD record
ord-badfb920f6794f76916d9157a13ee71c
Source dataset
uspto-grants-2006_07
Patent number
US07074831B2

Reaction notes

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