1,1'-Carbonyldiimidazole → 1-Benzylimidazolidin-2-one

HRID 23558

Reaction equation

HRID 23558 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12](N1C=CN=C1)(N1C=CN=C1)=[O:13]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH2:10][NH:11][C:12]1=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 77801N-Benzylethylenediamine

Product 1

HCID 2314031-Benzylimidazolidin-2-oneYield 49.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-benzylethylenediamine (6.0 g, 40 mmol) in toluene (50 ml) at 0° C. was added 1,1′-carbonylbis-1H-imidazole (7.8 g, 48 mmol). After stirring the mixture at room temperature overnight, the reaction mixture was washed with water, 5% aqueous citric acid solution and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was recrystallized with warm ethyl acetate and filtered off to give 1-benzylimidazolidin-2-one (3.47 g).

Workup

  1. washthe reaction mixture was washed with water, 5% aqueous citric acid solution and brine
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallized with warm ethyl acetate
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-25f7d1db2d0b40efa6b910d5b1689781
Source dataset
uspto-grants-2005_02
Patent number
US06852744B2

Linked notes

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