Benzyl bromoacetate → HCID 53926892, compound

HRID 274225Notes

Reaction equation

HRID 274225 reaction equation
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH:7]=[C:8]2[NH:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])=[CH:5][CH:4]=1)#[N:2].CC([O-])(C)C.[K+].Br[CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[C:8]2[NH:12][C:11](=[O:13])[N:10]([CH2:24][C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[C:9]2=[O:14])=[CH:15][CH:16]=1)#[N:2]

Participants

5

Reactant 3

HCID 62576Benzyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 541420304-[(2,5-Dioxoimidazolidin-4-ylidene)methyl]benzonitrile

Product 1

HCID 53926892HCID 53926892, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.4 g (0.03 mol) of (5-(4-cyanobenzylidene)-2,4-dioxoimidazolidine and 3.5 g (0.031 mol) of potassium tert-butylate are dissolved in 30 ml of dimethylformamide. After addition of 7.1 g (0.031 mol) of benzyl bromoacetate, the mixture is stirred at room temperature for 7 hours, heated briefly to 100° C. and concentrated. Water is added to the residue, and the mixture is extracted with ethyl acetate. The product crystallises out of the ethyl acetate phase, or can be precipitated by addition of heptane.

Workup

  1. temperatureheated briefly to 100° C.
  2. concentrationconcentrated
  3. additionWater is added to the residue
  4. extractionthe mixture is extracted with ethyl acetate
  5. customThe product crystallises out of the ethyl acetate phase
  6. customcan be precipitated by addition of heptane

Sources & evidence

ORD record
ord-de20046081614173bde1c52f0c7cde91
Source dataset
uspto-grants-1995_02
Patent number
US05389614

Reaction notes

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