Azobisisobutyronitrile → HCID 21949876, compound

HRID 2215328Notes

Reaction equation

HRID 2215328 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([O:18][C:19]2[C:20]([CH3:26])=[N:21][N:22]([CH3:25])[C:23]=2[CH3:24])[CH:17]=1)[C:13]#[N:14].N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:24][C:23]1[N:22]([CH3:25])[N:21]=[C:20]([CH3:26])[C:19]=1[O:18][C:16]1[CH:15]=[C:12]([CH:11]=[C:10]([Cl:9])[CH:17]=1)[C:13]#[N:14]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 21949889HCID 21949889, compound

Product 1

HCID 21949876HCID 21949876, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (340 mg, 1.90 mmol) was added to a stirred solution of the pyrazole of Example 112 (500 mg, 1.90 mmol) in carbon tetrachloride (10 ml) and azobisisobutyronitrile (20 mg) at room temperature under nitrogen. The reaction was heated under reflux for 1 hour, cooled to room temperature and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel eluting with pentane:ethyl acetate (80:20, by volume) to provide the title compound (340 mg) as a white solid, m.p. 76–78° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 1 hour
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by flash column chromatography on silica gel eluting with pentane:ethyl acetate (80:20, by volume)

Sources & evidence

ORD record
ord-57218a04a86d4ec5a664dc6c66c493f3
Source dataset
uspto-grants-2006_09
Patent number
US07109228B2

Reaction notes

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