Diisopropyl Ether → HCID 57216960, compound

HRID 912480Notes

Reaction equation

HRID 912480 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]1[NH:12][C:10](=[O:11])[NH:9][CH2:8]1.Br[CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1.C(OC(C)C)(C)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH3:22][O:21][C:19]([C:18]1[CH:23]=[CH:24][C:15]([CH2:14][N:9]2[CH2:8][CH2:7][NH:12][C:10]2=[O:11])=[CH:16][CH:17]=1)=[O:20]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 84532-ImidazolidinoneHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 57216960HCID 57216960, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (7.88 g; 57 mmol) was added to a solution of 4.92 g of ethylene urea (57 mmol), 5.73 g of methyl 4-bromomethylbenzoate (25 mmol) and 1.85 g of tetra-n-butylammonium iodide (5.0 mmol) in 30 mL of DMF, and the mixture was heated with stirring at 80° C. for 5 hours. After cooling, the solid was collected by filtration and washed with ethyl acetate. The filtrate was concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate:methanol=10:1). To the light yellow oil obtained was added diisopropyl ether, and the precipitated solid was collected by filtration and dried to give 3.36 g of N-(4-methoxycarbonylphenylmethyl)imidazolin-2-one (Yield: 57.4%) as a light brown solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. filtrationthe solid was collected by filtration
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate:methanol=10:1)
  7. customTo the light yellow oil obtained
  8. filtrationthe precipitated solid was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-956d62eec17f493089b81c4beff08272
Source dataset
uspto-grants-2011_09
Patent number
US08026239B2

Reaction notes

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