Azobisisobutyronitrile → HCID 117770794, compound

HRID 1526337Notes

Reaction equation

HRID 1526337 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:4](=[O:16])[C:3]=1[C:17]#[N:18].[Br:19]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.ClCCl>[Br:19][CH2:8][C:6]1[N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:4](=[O:16])[C:3]([C:17]#[N:18])=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 117770287HCID 117770287, compound

Product 1

HCID 117770794HCID 117770794, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-1-(2-chlorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step E (1.55 g) in carbon tetrachloride (69.4 mL) were added N-bromosuccinimide (1.19 g) and 2,2′-azobis(isobutyronitrile) (0.0910 g) at room temperature. The reaction mixture was refluxed for 3 hr, and cooled to room temperature. The reaction mixture was diluted with dichloromethane, and the mixture was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.23 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hr
  2. washthe mixture was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4815c41edbe141858921601c4fc5a448
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

Loading…