1-Bromononane → HCID 512846, compound

HRID 1016522Notes

Reaction equation

HRID 1016522 reaction equation
[CH2:1]([CH:3]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[CH2:4]1)[CH3:2].[H-].[Na+].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>>[CH2:1]([CH:3]1[C:8](=[O:9])[N:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:5](=[O:6])[CH2:4]1)[CH3:2]

Participants

4

Reactant 3

HCID 127421-BromononaneHCID 24758Sodium hydrideHCID 126481913-Ethylpyrrolidine-2,5-dione

Product 1

HCID 512846HCID 512846, compound

Procedure

A solution of 3-ethyl succinimide (4.72 mM) in dimethylformanide (10 ml) was treated with sodium hydride (5.20 mM) and nonyl bromide (5.20 mM). The reaction mixture was stirred at room temperature for two hours and then quenched with saturated aqueous ammonium chloride. The organic layer was separated and the aqueous layer extracted with ethyl acetate(3×25 ml). The combined organic layers were washed with 10% aqueous sodium thiosulfate, brine, dried over sodium sulfate and concentrated in vacuo. Chromatography over silica gel afforded the desired product, pure 3-ethylN-nonyl succinimide.

Workup

  1. customquenched with saturated aqueous ammonium chloride
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with ethyl acetate(3×25 ml)
  4. washThe combined organic layers were washed with 10% aqueous sodium thiosulfate, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3688d5c5504940e3830d7d184821a791
Source dataset
uspto-grants-2002_11
Patent number
US06476053B1

Reaction notes

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