Ethyl Acetate → 1-(Meta-tolyl)-2-imidazolidinone

HRID 80168Notes

Reaction equation

HRID 80168 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=1)=[O:6].[H-].[Na+].C(OC(=O)C)C>CN(C=O)C.C1COCC1>[C:10]1([CH3:14])[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 97216Urea, 1-(2-chloroethyl)-3-(m-tolyl)-

Product 1

HCID 43049911-(Meta-tolyl)-2-imidazolidinoneYield 81.34%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Chloro-ethyl)-3-m-tolyl-urea (I-131a: 4 g, 18.86 mmol) in dry DMF (70 mL) was added to a stirred mixture of sodium hydride (1.358 g, 28.30 mmol) in THF (70 mL) at 0° C. The reaction was stirred at room temperature for 1 hour. The reaction was monitored by TLC (100% ethylacetate). The reaction mixture was quenched with MeOH at 0° C., concentrated under reduced pressure and partitioned between ice water and chloroform. The organic layer was washed with brine solution, dried over Na2SO4, and concentrated under reduced pressure to afford 2.7 g (81.34% yield) of 1-m-tolyl-imidazolidin-2-one.

Workup

  1. customThe reaction mixture was quenched with MeOH at 0° C.
  2. concentrationconcentrated under reduced pressure
  3. custompartitioned between ice water and chloroform
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a4af7ba97ded431c97f7172b897a3f21
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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