1,3-Dibromo-5,5-dimethylhydantoin → HCID 22008912, compound

HRID 322009Notes

Reaction equation

HRID 322009 reaction equation
[Br:1]N1C(C)(C)C(=O)N(Br)C1=O.[CH3:12][O:13][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16]([Cl:23])[C:15]=1[CH3:24].C(OCC)(=O)C>ClC1C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:12][O:13][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16]([Cl:23])[C:15]=1[CH2:24][Br:1]

Participants

6

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoin2×HCID 8857Ethyl AcetateHCID 22008918HCID 22008918, compound

Product 1

HCID 22008912HCID 22008912, compoundYield 181.8%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalyst2×HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 5.8 g (20.0 mmol) of 1,3-dibromo-5,5-dimethylhydantoin and 0.5 g of azobisisobutyronitrile was added in portions at 110° C. to a solution of 8.0 g (40.0 mmol) of 2-methoxy-6-chloro-3-nitrotoluene from Example 11aα) in 50 ml of chlorobenzene. After 1 h, a mixture of 3.0 g (10 mmol) of 1,3-dibromo-5,5-dimethylhydantoin and 0.2 g of azobisisobutyronitrile was again added. After a further 1.5 h, the mixture was allowed to cool, and 500 ml of ethyl acetate were added to the reaction solution. The resulting mixture was washed once each with satd Na2SO3 solution, Na2CO3 solution, and NaCl solution, dried (MgSO4), and concentrated. 10.2 g of the title compound resulted in the form of an amorphous powder.

Workup

  1. additionwas again added
  2. waitAfter a further 1.5 h
  3. temperatureto cool
  4. washThe resulting mixture was washed once each with satd Na2SO3 solution, Na2CO3 solution, and NaCl solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f5d466a23c8246e68a0b4120079f8ab1
Source dataset
uspto-grants-2001_04
Patent number
US06211196B1

Reaction notes

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