Potassium Carbonate → 3-[(4-Bromophenyl)methyl]-1-methylimidazolidine-2,4-dione

HRID 1891260Notes

Reaction equation

HRID 1891260 reaction equation
[CH3:1][N:2]1[CH2:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16]Br)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:4]2[C:5](=[O:7])[CH2:6][N:2]([CH3:1])[C:3]2=[O:8])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 692171-Methylhydantoin

Product 1

HCID 606247733-[(4-Bromophenyl)methyl]-1-methylimidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Methylimidazolidine-2,4-dione (0.876 mmol, 100 mg), 1-bromo-4-(bromomethyl)benzene (0.964 mmol, 241 mg) and potassium carbonate (1.75 mmol, 242 mg) in acetonitrile (3 ml) were heated in the microwave at 120° C. for 1 h. The mixture was partitioned between water and DCM and the organic phase separated using a hydrophobic frit and concentrated to afford 3-(4-bromobenzyl)-1-methylimidazolidine-2,4-dione (3D3); 1H NMR (400 MHz, CDCl3) δ 7.44 (d, 2H) 7.29 (d, 2H) 4.59 (s, 2H) 3.85 (s, 2H) 2.98 (s, 3H).

Workup

  1. customThe mixture was partitioned between water and DCM
  2. customthe organic phase separated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-51798dcc25894f008d5355e6206e6c5e
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

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