Azobisisobutyronitrile → HCID 18771988, compound

HRID 460171Notes

Reaction equation

HRID 460171 reaction equation
[C:1]([N:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][CH:8]1[NH2:14])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C1C(=O)N([Br:22])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[C:1]([N:7]1[CH:12]=[C:11]([CH2:13][Br:22])[CH:10]=[CH:9][CH:8]1[NH2:14])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 18771903HCID 18771903, compound

Product 1

HCID 18771988HCID 18771988, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Pivaloyl-2-amino-5-methylpyridine (5.12 g, 26.6 mmol) was dissolved in CCl4 (75 mL) at 23° C., and treated with NBS (9.69 g, 54.4 mmol), followed by AIBN (937 mg, 5.71 mmol) with stirring. The resulting orange, biphasic suspension was then warmed to reflux for 4 h. After 4 h at reflux, the rust-colored mixture was cooled to RT, filtered through a Celite® pad, and concentrated in vacuo to a red residue. Purification over silica gel (gradient, 0 to 25% EtOAc/hexanes) provided the title compound as a light yellow solid. MS m/z: 272 (M+H).

Workup

  1. temperatureThe resulting orange, biphasic suspension was then warmed
  2. temperatureto reflux for 4 h
  3. temperatureAfter 4 h at reflux
  4. filtrationfiltered through a Celite® pad
  5. concentrationconcentrated in vacuo to a red residue
  6. customPurification over silica gel (gradient, 0 to 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9fe7da443caf41d59c9cf798d17d69ed
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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