1,3-Dibromo-5,5-dimethylhydantoin → HCID 58102920, compound

HRID 389629Notes

Reaction equation

HRID 389629 reaction equation
[CH:1]1([N:4]2[CH:8]=[CH:7][N:6]=[CH:5]2)[CH2:3][CH2:2]1.[Br:9]N1C(C)(C)C(=O)N(Br)C1=O>C(Cl)Cl>[Br:9][C:8]1[N:4]([CH:1]2[CH2:3][CH2:2]2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 100346031H-IMidazole, 1-cyclopropyl-

Product 1

HCID 58102920HCID 58102920, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
7.5 °C

Procedure

Cyclopropyl-1H-imidazole (1.18 g, 10.9 mmol) was dissolved in methylene chloride (0.1 M), cooled to 5-10° C., and 1,3-dibromo-5,5-dimethylhydantoin (1.59 g, 5.57 mmol) was added. The temperature was maintained between 5-10° C. and the reaction was stirred for 2 hours. Solvent was removed from the reaction mixture under reduced pressure, and the residue was purified by column chromatography (eluting with 1%-7% methanol in methylene chloride, 5% methanol/methylene chloride) to afford 620 mg (37% yield) of 5-bromo-1-cyclopropyl-1H-imidazole.

Workup

  1. temperatureThe temperature was maintained between 5-10° C.
  2. customSolvent was removed from the reaction mixture under reduced pressure
  3. customthe residue was purified by column chromatography (eluting with 1%-7% methanol in methylene chloride, 5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-119361dd65c34f9c81e6dd0b8a851c76
Source dataset
uspto-grants-2013_02
Patent number
US08378108B2

Reaction notes

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