Dimethylformamide → 1-decylpyrrolidine-2,5-dione

HRID 1016507Notes

Reaction equation

HRID 1016507 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH2:3][CH2:2]1.[H-].[Na+].[CH2:10](Br)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:20]N(C)C=O>>[CH2:18]([N:5]1[C:4](=[O:6])[CH2:3][CH2:2][C:1]1=[O:7])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:20]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11439SuccinimideHCID 127421-BromononaneHCID 24758Sodium hydride

Product 1

HCID 2201041-decylpyrrolidine-2,5-dione

Procedure

Succinimide (0.1 M) dissolved in dry dimethylformamide was treated with sodium hydride (0.1 M) at a temperature of 0° C. Nonyl bromide (0.1 M) was then added and the reaction mixture was stirred at room temperature for three hours. The reaction mixture was concentrated in vacuo and the residue extracted into ethyl acetate. The ethyl acetate layer was washed with water, dried over sodium sulphate and concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product. 1HNMR: δ 0.75 (3H, t), 1.10-1.20 (12H, m), 1.35-1.45 (2H, m), 2.55 (4H, s), 3.35 (2H, dd)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionthe residue extracted into ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-0d88568459ce4a4284c6a6db5a64feae
Source dataset
uspto-grants-2002_11
Patent number
US06476053B1

Reaction notes

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