Azobisisobutyronitrile → HCID 58910028, compound

HRID 1295925Notes

Reaction equation

HRID 1295925 reaction equation
[C:1]([C:3]1[C:4]([CH3:23])=[CH:5][C:6]([O:20][CH2:21][CH3:22])=[C:7]([CH:19]=1)[C:8]([N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:9])#[N:2].N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:36]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:36][CH2:23][C:4]1[C:3]([C:1]#[N:2])=[CH:19][C:7]([C:8]([N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:9])=[C:6]([O:20][CH2:21][CH3:22])[CH:5]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 22929887HCID 22929887, compound

Product 1

HCID 58910028HCID 58910028, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

After dissolving tert-butyl N-(5-cyano-2-ethoxy-4-methylbenzoyl)-N-methylcarbamate (79.6 g) in carbon tetrachloride, azobisisobutyronitrile (4.1 g) was added and the mixture was heated to reflux. N-bromosuccinimide (50.3 g) was gradually added to the reaction mixture in small portions at a time. After heating to reflux for 2 hours, the mixture was filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (29.81 g) as a white solid.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated to reflux
  3. temperatureAfter heating
  4. temperatureto reflux for 2 hours
  5. filtrationthe mixture was filtered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-3d769727094a4cdab7244a525592345b
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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