N-bromobutanimide → HCID 23155534, compound

HRID 2080803Notes

Reaction equation

HRID 2080803 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:3]=1.[Br:15]N1C(=O)CCC1=O>N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:14][C:11]1[CH:10]=[CH:9][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[N:3]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 23155520Pyridine, 2-chloro-6-(4-methylphenyl)-

Product 1

HCID 23155534HCID 23155534, compoundYield 275%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

The mixture (4.02 g) obtained in Example 36-1 in a carbon tetrachloride solution (45 ml) was added with N-bromosuccinimide (1.31 g) and 2,2′-azobisisobutyronitrile (0.121 g) and the whole was refluxed for 30 minutes. After that, the solution was cooled to room temperature and a solid component was separated by filtration. The organic layer was washed with a 1 mol/l sodium hydroxide aqueous solution and a saturated saline solution in the stated order, and dried with anhydrous magnesium sulfate. The solvent was distilled off and dried under reduced pressure, thereby obtaining a mixture (5.72 g) containing the subject compound.

Workup

  1. temperaturethe whole was refluxed for 30 minutes
  2. customa solid component was separated by filtration
  3. washThe organic layer was washed with a 1 mol/l sodium hydroxide aqueous solution
  4. dry with materiala saturated saline solution in the stated order, and dried with anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-51ca0b09917a4ec7b22ad7aec9c7e9b1
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

Loading…