Propyphenazone → HCID 12883634, compound

HRID 1993927Notes

Reaction equation

HRID 1993927 reaction equation
[CH:1]([C:4]1[C:5](=[O:17])[N:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]([CH3:10])[C:8]=1[CH3:9])([CH3:3])[CH3:2].[Br:18]Br>O1CCOCC1.O.CCOC(C)=O>[Br:18][CH2:9][C:8]1[N:7]([CH3:10])[N:6]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:5](=[O:17])[C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 3778PropyphenazoneHCID 24408Bromine

Product 1

HCID 12883634HCID 12883634, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To 4-isopropyl-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (0.8 g) in a round bottom flask under argon in dioxane (15 mL) was added bromine (0.55 g). The reaction was stirred at ambient temperature for 5 hours. The reaction was diluted with water and EtOAc and the phases were separated. The aqueous phase was extracted with more EtOAc and the combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo. The crude material was purified via ISCO combiflash chromatography (EtOAc/heptane) to afford the desired 5-bromomethyl-4-isopropyl-1-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one as a light brown solid. MS (ESI+): 309.3 ([M+H]+).

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with more EtOAc
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude material was purified via ISCO combiflash chromatography (EtOAc/heptane)

Sources & evidence

ORD record
ord-3f8b1c97378c49c7ae4d3c07f992b445
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

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