N-bromobutanimide → HCID 23303000, compound

HRID 1953132Notes

Reaction equation

HRID 1953132 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]#[N:9].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:10][CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:8]#[N:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 75959Pyridine-2-acetonitrile

Product 1

HCID 23303000HCID 23303000, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of (2-pyridyl)acetonitrile (12.0 g, 0.10 mole) in 150 ml of carbon tetrachloride, was added 18.1 g of N-bromosuccinimide (0.10 mole) at room temperature. The mixture was refluxed for 1.5 h. The resulting precipitate was removed by filtration and the solvent was removed under reduced pressure to give the crude product, which was recrystallized from hexane to yield 18.6 g (94%) of the title compound as red crystals:

Workup

  1. temperatureThe mixture was refluxed for 1.5 h
  2. customThe resulting precipitate was removed by filtration
  3. customthe solvent was removed under reduced pressure
  4. customto give the crude product, which
  5. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-d6ce70ea7a0b4c71b4d640d741278539
Source dataset
uspto-grants-2000_09
Patent number
US06114537

Reaction notes

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