Azobisisobutyronitrile → (2E)-2-[2-(bromomethyl)phenyl]-2-methoxyimino-N-methylacetamide

HRID 1441162Notes

Reaction equation

HRID 1441162 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])/[C:5]([NH:7][CH3:8])=[O:6].C1C(=O)N([Br:23])C(=O)C1.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1/[C:4](=[N:3]\[O:2][CH3:1])/[C:5]([NH:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 59915423(2E)-2-methoxyimino-N-methyl-2-(2-methylphenyl)acetamide

Product 1

HCID 15239358(2E)-2-[2-(bromomethyl)phenyl]-2-methoxyimino-N-methylacetamideYield 37.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To (E)-2-methoxyimino-2-(2-methylphenyl)-N-methylacetamide (2.66 g, 0.01 mol), added were carbon tetrachloride (20 ml), NBS (1.96 g, 0.011 mol) and α,α'-azobis(isobutyronitrile) (0.16 g, 0.001 mol), and the reaction mixture was heated under reflux for 1 hour. After completion of the reaction, undissolved materials were removed and the remaining mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/toluene) to give (E)-2-(2-bromomethylphenyl)-2-methoxyimino-N-methylacetamide (1.08 g; yield, 37.7%) as an oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customAfter completion of the reaction, undissolved materials
  4. customwere removed
  5. concentrationthe remaining mixture was concentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/toluene)

Sources & evidence

ORD record
ord-eeaee13b811b41c1880675cef104dea8
Source dataset
uspto-grants-1996_03
Patent number
US05502252

Reaction notes

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