Potassium Carbonate → 1-(4-Bromo-benzyl)-3-cyclobutylmethyl-imidazolidine-2,4-dione

HRID 2423060Notes

Reaction equation

HRID 2423060 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.Br[CH2:17][CH:18]1[CH2:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>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]([CH2:17][CH:18]3[CH2:21][CH2:20][CH2:19]3)[C:8]2=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734658(Bromomethyl)cyclobutaneHCID 154067221-(4-Bromobenzyl)imidazolidine-2,4-dione

Product 1

HCID 668136401-(4-Bromo-benzyl)-3-cyclobutylmethyl-imidazolidine-2,4-dioneYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

i)—To a solution of 1-(4-bromo-benzyl)imidazolidine-2,4-dione (Example 4, step iii) (5.91 g, 21.96 mmol) in DMF (50 ml) were added (bromomethyl)cyclobutane (6.55 g, 43.9 mmol) and potassium carbonate (9.11 g, 65.9 mmol) under a nitrogen atmosphere. After stirring for 20 h at room temperature, the reaction mixture was concentrated under reduced pressure. The product was extracted in ethyl acetate and the combined organic layers were washed with water, brine, dried over sodium sulfate and concentrated under reduced pressure to give 1-(4-bromo-benzyl)-3-cyclobutylmethyl-imidazolidine-2,4-dione (5.30 g).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. extractionThe product was extracted in ethyl acetate
  3. washthe combined organic layers were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f13ae18389c542a1a66eeaf04c58b0c4
Source dataset
uspto-grants-2011_06
Patent number
US07960560B2

Reaction notes

Loading…