2-Pyrrolidone → HCID 19875247, compound

HRID 465696Notes

Reaction equation

HRID 465696 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:12][C:13]#[N:14])[C:9](Cl)=[O:10])=[CH:4][CH:3]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][C:16]1=O.[H-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]#[N:14])=[C:16]3[CH2:17][CH2:18][CH2:19][N:15]3[C:9]2=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 19875268HCID 19875268, compound

Product 1

HCID 19875247HCID 19875247, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-(4-chlorophenyl)-N-cyanomethylcarbamoyl chloride, prepared as described in Example 53, (2.7 g, 0.012 mol) was dissolved in 10 mL of dimethylformamide and added dropwise to a cold solution (0° C.) of 2-pyrrolidinone (1.0 g, 0.012 mol) and sodium hydride (0.96 g, 0.024 mol) in 20 mL of DMF. The solution was allowed to warm to ambient temperature over two hours, then it was poured onto ice water and extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over magnesium sulfate, and concentrated to yield an oil. Elution of this oil through a silica gel column using 1:2 ethyl acetate:hexane furnished 0.4 g of 2-(4-chlorophenyl)-2,3,6,7-tetrahydro-3-oxo-5H-pyrrolo-[l,2-c]imidazol-1-carbonitrile, as a solid (m.p. 154°-6° C.).

Workup

  1. additionit was poured onto ice water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto yield an oil
  7. washElution of this oil through a silica gel column

Sources & evidence

ORD record
ord-a9f4bc0f04d14dd4bfc45ec4e58f3494
Source dataset
uspto-grants-1992_10
Patent number
US05153316

Reaction notes

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