Azobisisobutyronitrile → HCID 18549818, compound

HRID 649823Notes

Reaction equation

HRID 649823 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=[N:9]1.[Br:17]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=[N:9]1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 18549820HCID 18549820, compound

Product 1

HCID 18549818HCID 18549818, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 1-[2-methylphenyl]pyrazole-5-carboxylate (1.00 g, 4.62 mmol) in 20 mL of carbon tetrachloride was added N-bromosuccinimide (0.823 g, 4.62 mmol) and AIBN (76 mg, 0.46 mmol). This mixture was stirred at 80° C. for 18 h. The volatiles were removed and the residue was taken up in ether, filtered through a pad of silica gel and concentrated to afford 1.3 g (95%) of the title compound which was used without further purification. LRMS (ES+): 295.0/297.0 (M+H)+.

Workup

  1. customThe volatiles were removed
  2. filtrationfiltered through a pad of silica gel
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-221a3926146c47498809d9b46efa88ff
Source dataset
uspto-grants-2001_08
Patent number
US06271237B1

Reaction notes

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