Anisole → HCID 19973527, compound

HRID 1452070Notes

Reaction equation

HRID 1452070 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH2:5][NH:4][C:3]1=[O:8].BrBr.[C:11]1([O:17][CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)(=O)C>[CH3:18][O:17][C:11]1[CH:16]=[CH:15][C:14]([CH:5]2[NH:4][C:3](=[O:8])[N:2]([CH3:1])[C:6]2=[O:7])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 24408BromineHCID 1388512,4-Imidazolidinedione, 3-methyl-

Product 1

HCID 19973527HCID 19973527, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

4.56 g (40 mmol) of 3-methyl-hydantoin, 30 ml of acetic acid, and 2.0 ml (40 mmol) of bromine were mixed at room temperature. The reaction mixture was then vigorously stirred at a temperature of 40° C. for 2 hours. The reaction mixture was then allowed to cool to room temperature. To the reaction mixture was then added 60 mmol of anisole. The reaction mixture was then allowed to undergo reaction at a temperature of 100° C. for 6 hours. The resulting precipitate was recovered by filtration, washed with water, and then dried to obtain 4.22 g (yield: 48%) of 5-(p-methoxyphenyl)-3-methyl-hydantoin.

Workup

  1. temperatureto cool to room temperature
  2. customreaction at a temperature of 100° C. for 6 hours
  3. filtrationThe resulting precipitate was recovered by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-1c0eaff459794c449970c73447ab73b3
Source dataset
uspto-grants-1997_02
Patent number
US05606071

Reaction notes

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