N-bromobutanimide → HCID 57656437, compound

HRID 911605Notes

Reaction equation

HRID 911605 reaction equation
[CH:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C(=O)N([Br:23])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[CH:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][Br:23])=[CH:11][CH:10]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 76035Cyclohexyl p-tolyl ketone

Product 1

HCID 57656437HCID 57656437, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalyst2×HCID 5943Carbon TetrachlorideSolvent

Procedure

Heat a mixture of cyclohexyl-p-tolyl-methanone (1 g, 4.943 mmol), NBS (1.232 g, 6.92 mmol), and AIBN (41 mg, 0.247 mmol) in carbon tetrachloride (80 mL) for 14 h at reflux. Add additional NBS (264 mg) and AIBN (19 mg) and reflux the mixture for 4 h. Cool the reaction mixture to ambient temperature and filter. Concentrate the filtrate in vacuo to provide the desired intermediate as oil (1.132 g, 81%) that was used without any further purification.

Workup

  1. temperatureHeat
  2. temperatureat reflux
  3. temperaturereflux the mixture for 4 h
  4. filtrationfilter
  5. concentrationConcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-08fefaf820fd4f728d5b7f03d393c85b
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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