Benzoyl Peroxide → HCID 58055787, compound

HRID 408869Notes

Reaction equation

HRID 408869 reaction equation
[C:1]([NH:5][C:6]([N:8]1[CH:12]=[CH:11][C:10]([CH3:13])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.O.C(OCC)(=O)C>[Br:14][CH2:13][C:10]1[CH:11]=[CH:12][N:8]([C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[N:9]=1

Participants

7

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 58055788HCID 58055788, compound

Product 1

HCID 58055787HCID 58055787, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To N-tert-butyl-3-methyl-1H-pyrazole-1-carboxamide (609 mg, 3.36 mmol) in carbon tetrachloride (12 mL) was added N-bromosuccinimide (849 mg, 4.77 mmol) and benzoyl peroxide (114 mg, 0.470 mmol). The mixture was heated to reflux overnight and then diluted with water and ethyl acetate. The organic layer was separated, dried and concentrated under reduced pressure. The crude material was purified by silica chromatography (eluting with 10% ethyl acetate in heptane) to give the title compound (280 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica chromatography (eluting with 10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-ae53b9be48de43faa61183328d69fe34
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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