N-bromobutanimide → HCID 23303000, compound

HRID 2289585Notes

Reaction equation

HRID 2289585 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: mp 62-64° C.; 1H NMR (DMSO-d6) δ8.67 (d, 1H), 7.97 (t, 1H), 7.70 (d, 1H), 7.51 (td, 1H), 5.60(s,1H) ppm; IR (KBr) ν 3064, 2972, 1712, 1587, 1470, 1439, 1051, 993 cm-1 ; MS m/z 196, 198 (M+), 117 (M+ -Br); HRMS calcd for C7H5BrN2 195.9630, found 195.9645.

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-1a147e4ddb584957803257ef4f021c26
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

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