N,N-Dimethylaniline → 1-(4-Bromo-3-methylphenyl)imidazolidine-2,4-dione

HRID 1754997Notes

Reaction equation

HRID 1754997 reaction equation
C(O[C:4](=[O:10])[NH:5][C:6](=[O:9])[CH2:7]Cl)C.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=1[CH3:19].CN(C)C1C=CC=CC=1>>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:7][C:6](=[O:9])[NH:5][C:4]2=[O:10])=[CH:14][C:13]=1[CH3:19]

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 233594-Bromo-3-methylanilineHCID 233830Ethyl (2-chloroacetyl)carbamate

Product 1

HCID 668172481-(4-Bromo-3-methylphenyl)imidazolidine-2,4-dioneYield 54.3%

Conditions

Temperature
130 °C

Procedure

(2-Chloro-acetyl)-carbamic acid ethyl ester (356 mg, 2.15 mmol) was added to 4-bromo-3-methyl-phenylamine (400 mg, 2.15 mmol) and dimethylphenylamine (273 μL, 2.15 mmol) at room temperature. The mixture was stirred at 130° C. for five hours, and the reaction solution was then cooled. The precipitate was collected by filtration and washed with CH3CN to give 1-(4-bromo-3-methyl-phenyl)-imidazolidine-2,4-dione as a colorless solid (314 mg, 54%).

Workup

  1. temperaturethe reaction solution was then cooled
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with CH3CN

Sources & evidence

ORD record
ord-ed756dc7acad497e895b2d30ba48b253
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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