Azobisisobutyronitrile → HCID 86678960, compound

HRID 2203313Notes

Reaction equation

HRID 2203313 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:3]=1.[Br:14]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:14][C:7]([C:4]1[N:3]=[C:2]([CH3:1])[O:6][N:5]=1)([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 10773832HCID 10773832, compound

Product 1

HCID 86678960HCID 86678960, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A carbon tetrachloride (30 mL) solution containing the intermediate from Step B (1.9 g, 10.3 mmol), N-bromosuccinimide (3.56 g, 20 mmol) and AIBN (0.1 g) was heated at reflux for 4 hours. The solution was cooled to room temperature, filtered and concentrated. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. m/z=263.0 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. customto give the indicated product

Sources & evidence

ORD record
ord-23a2494acd364c36b7b4f31f99b0a0d5
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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