Dimethylformamide → HCID 59750207, compound

HRID 748441Notes

Reaction equation

HRID 748441 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[O:14])=[CH:5][CH:4]=1.CN(C=O)C.Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>O>[O:14]=[C:10]1[N:9]([C:6]2[CH:5]=[CH:4][N:3]=[CH:8][CH:7]=2)[CH2:13][CH2:12][N:11]1[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 37468181-Pyridin-4-yl-imidazolidin-2-one

Product 1

HCID 59750207HCID 59750207, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% in oil, 0.40 g, 10.1 mmol) was added to a mixture of 1-(4-pyridyl)-2-imidazolidinone (1.5 g, 9.2 mmol) and DMF (20 ml) at 0° C., and the mixture was stirred at room temperature for 30 minutes. Successively, tert-butyl bromoacetate (2.2 g, 11.2 mmol) was added to the mixture, and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was combined with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-methanol (5:1, v/v) were collected, concentrated and recrystallized from tetrahydrofuran-hexane to give the titled compound (1.7 g, 68%) as white crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hrs
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. washThe fractions eluted with ethyl acetate-methanol (5:1
  7. customv/v) were collected
  8. concentrationconcentrated
  9. customrecrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-69add02ce25b481bad78f87256fd2df4
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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