Chloroacetamide → Ethyl 2,5-dioxo-3-pyrrolidinecarboxylate

HRID 483104

Reaction equation

HRID 483104 reaction equation
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl[CH2:15][C:16]([NH2:18])=[O:17]>CN(C)C=O>[CH2:6]([O:5][C:3]([CH:2]1[CH2:15][C:16](=[O:17])[NH:18][C:1]1=[O:9])=[O:4])[CH3:7]

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 7761Diethyl MalonateHCID 24758Sodium hydride

Product 1

HCID 23635561Ethyl 2,5-dioxo-3-pyrrolidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of diethyl malonate (6.1 ml) in N,N-dimethylformamide (30 ml) are added 60% sodium hydride (1.6 g) at 0° C. and, after 8 minutes, chloroacetamide (1.87 g). After stirring at room temperature for 3.5 hours, the mixture in neutralized with acetic acid and extracted with ethyl acetate. The extract is washed with water and concentrated to give 2,5-dioxopyrrolidine-3-carboxylic acid ethyl ester. Oil.

Workup

  1. extractionthe mixture in neutralized with acetic acid and extracted with ethyl acetate
  2. washThe extract is washed with water
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a315d93cc0df448580a90e1858c3b76d
Source dataset
uspto-grants-1986_03
Patent number
US04578378

Linked notes

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