Acetic Acid → 1-(Pyridin-3-yl)imidazolidin-2-one

HRID 476993Notes

Reaction equation

HRID 476993 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:6].[H-].[Na+].C(O)(=O)C>CN(C)C=O>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])[CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 256330N-(2-Chloroethyl)-N'-(3-pyridinyl)urea

Product 1

HCID 148342041-(Pyridin-3-yl)imidazolidin-2-oneYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 150 g of N-(2-chloroethyl)-N'-(3-pyridyl) urea dissolved in 500 ml of tetrhydrofuran and 500 ml of dimethylformamide, 31.6 g of sodium hydride (60% oily suspension) was added under ice-cooling over 20 minutes. After stirring under ice-cooling for 10 minutes and at room temperature for 2 hours, 10 ml of acetic acid was added and the solvent was distilled off. Saturated saline water and chloroform were added to thr residue and insolubles were separated by filtration. The chloroform layer was washed with sodium hydrogen carbonate solution, dried and the solvent was distilled off. The residue was recrystallized from a mixture of chloroform and hexane to give 108.5 g of 1-(3-pyridyl)-2-imidazolidinone.

Workup

  1. additionwas added under ice-
  2. temperaturecooling over 20 minutes
  3. distillationthe solvent was distilled off
  4. additionSaturated saline water and chloroform were added to thr residue and insolubles
  5. customwere separated by filtration
  6. washThe chloroform layer was washed with sodium hydrogen carbonate solution
  7. customdried
  8. distillationthe solvent was distilled off
  9. customThe residue was recrystallized from a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-5e860d279dab4a1891a62879ce7f19f4
Source dataset
uspto-grants-1989_12
Patent number
US04886817

Reaction notes

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