Dimethylformamide → 1-Pyridin-4-yl-imidazolidin-2-one

HRID 499622Notes

Reaction equation

HRID 499622 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)=[O:8].O1CCCC1.CN(C=O)C>CO>[N:13]1[CH:14]=[CH:15][C:10]([N:9]2[CH2:4][CH2:5][NH:6][C:7]2=[O:8])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 98728Urea, 1-(2-chloroethyl)-3-(p-pyridyl)-

Product 1

HCID 37468181-Pyridin-4-yl-imidazolidin-2-oneYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydride (60% in oil, 2.4 g, 60 mmol) was added to a mixture of N-(2-chloroethyl)-N′-(4-pyridyl)urea (11.1 g, 55 mmol), tetrahydrofuran (40 ml) and DMF (40 ml) at 0° C., and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was combined with methanol. The solvent was evaporated, and the residue was combined with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The residue was recrystallized from tetrahydrofuran-hexane to give the titled compound (2.4 g, 27%) as white crystals.

Workup

  1. customThe solvent was evaporated
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe residue was recrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-9646fdda65b540d4b2acb22fb3d97d46
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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