Ethyl Acetate → 1-(Pyridin-3-yl)imidazolidin-2-one

HRID 80022Notes

Reaction equation

HRID 80022 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(OCC)(=O)C>CN(C=O)C.C1COCC1>[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

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 256330N-(2-Chloroethyl)-N'-(3-pyridinyl)urea

Product 1

HCID 148342041-(Pyridin-3-yl)imidazolidin-2-oneYield 98.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Chloro-ethyl)-3-pyridin-3-yl-urea (I-1a: 1000 mg, 5.0 mmol) in dry DMF (10 mL) was added to a stirred solution of sodium hydride (216 mg, 9.0 mmol) in THF (10 mL) at 0° C. The reaction temperature was maintained at room temperature for 30 minutes. The reaction was monitored by TLC (100% ethyl acetate). The reaction mixture was quenched with MeOH (5 mL) at 0° C. The reaction mixture was concentrated under reduced pressure and partitioned between ice water and chloroform. The organic layer was dried over Na2SO4, and concentrated under reduced pressure to afford 800 mg (97% yield) of 1-pyridin-3-yl-imidazolidin-2-one.

Workup

  1. customThe reaction mixture was quenched with MeOH (5 mL) at 0° C
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompartitioned between ice water and chloroform
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8c6c6e245fdb4ac48d093b076fa36d97
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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