Azobisisobutyronitrile → HCID 57656325, compound

HRID 2041573Notes

Reaction equation

HRID 2041573 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([C:6]([C:5]2[CH:4]=[CH:3][C:2]([CH2:1][Br:25])=[CH:17][CH:16]=2)=[O:7])=[CH:9][CH:10]=1)#[N:13]

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide2×HCID 816842HCID 816842, compound

Product 1

HCID 57656325HCID 57656325, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Heat a mixture of 4-(4-methyl-benzoyl)-benzonitrile (300 mg, 1.356 mmol), NBS (386 mg, 2.169 mmol), and AIBN (22 mg, 0.136 mmol) in carbon tetrachloride (10 mL) for 14 h at reflux. Add additional NBS (121 mg) and AIBN (11 mg) and reflux the mixture for 3 h. Cool the reaction mixture to ambient temperature and filter the mixture. Concentrate the filtrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting sequentially with hexane and hexane/EtOAc (9:1) to provide the title compound as a solid (286 mg, 70%). GC-MS m/z: 300 (M+).

Workup

  1. temperatureHeat
  2. temperatureat reflux
  3. temperaturereflux the mixture for 3 h
  4. filtrationfilter the mixture
  5. concentrationConcentrate the filtrate in vacuo
  6. customPurify the crude mixture by chromatography on silica gel eluting sequentially with hexane and hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-173ca84e09064c919ad389f83cccec3a
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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