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Methyl iodide → 1-(4-Bromobenzyl)-3-methylimidazolidine-2,4-dione

HRID 1891255
Notes
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Reaction equation

HRID 1891255 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:11][C:10](=[O:12])[N:9]([CH3:16])[C:8]2=[O:13])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 154067221-(4-Bromobenzyl)imidazolidine-2,4-dione

Product 1

HCID 668132201-(4-Bromobenzyl)-3-methylimidazolidine-2,4-dioneYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1-(4-Bromobenzyl)imidazolidine-2,4-dione (1B4) (1.86 mmol, 500 mg) was dissolved in DMF (7 ml) and potassium carbonate (5.57 mmol, 770 mg) and iodomethane (1B5) (1.86 mmol, 0.116 ml, 264 mg) were added and the reaction mixture was stirred at 50° C. under nitrogen. The reaction was monitored by TLC and after 48 h of heating some starting material remained. An additional 2 equivalents of iodomethane (3.72 mmol, 0.232 ml, 528 mg) was added and the mixture stirred at 75° C. under nitrogen overnight. The reaction mixture was cooled to room temperature, filtrated and concentrated, then purified on silica eluting with heptane/EtOAc/EtOH 5/4/1 to give 1-(4-bromobenzyl)-3-methylimidazolidine-2,4-dione (1B6) 438 mg, (83%); 1H NMR (400 MHz, CDCl3) 7.51 (d, 2H) 7.15 (d, 2H) 4.53 (s, 2H) 3.74 (s, 2H) 3.06 (s, 3H).

Workup

  1. temperatureof heating some starting material
  2. stirringthe mixture stirred at 75° C. under nitrogen overnight
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. custompurified on silica eluting with heptane/EtOAc/EtOH 5/4/1

Sources & evidence

ORD record
ord-846543b8db8549048b3c8374cbea17aa
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08507521B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes