Water → N-(Cyanomethyl)-phthalimide

HRID 2359953Notes

Reaction equation

HRID 2359953 reaction equation
Br[CH2:2][C:3]#[N:4].[C:5]1(=[O:15])[NH:9][C:8](=[O:10])[C:7]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:6]12.[K].O>CN(C)C=O>[O:10]=[C:8]1[C:7]2[C:6](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5](=[O:15])[N:9]1[CH2:2][C:3]#[N:4]

Participants

5

Reactant 3

HCID 962WaterHCID 11534BromoacetonitrileHCID 24194345Phthalimide potassium salt

Product 1

HCID 345881N-(Cyanomethyl)-phthalimideYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of bromoacetonitrile (22 g) in N,N-dimethylformamide (200 mL) was added potassium phthalimide (34 g) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethanol to give the title compound as white crystals (yield 27 g, 80%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-9b2af5530590418a9317f083c18edc9a
Source dataset
uspto-grants-2014_04
Patent number
US08686010B2

Reaction notes

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