Chlorosuccinimide → 4-Chloro-5-isopropyl-3-trifluoromethylpyrazole

HRID 1372014Notes

Reaction equation

HRID 1372014 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[NH:5][N:4]=1.C1C(=O)N([Cl:20])C(=O)C1>CC#N>[Cl:20][C:7]1[C:3]([C:2]([F:1])([F:11])[F:12])=[N:4][NH:5][C:6]=1[CH:8]([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 230062143-(trifluoroMethyl)-5-isopropyl-1H-pyrazole

Product 1

HCID 210711494-Chloro-5-isopropyl-3-trifluoromethylpyrazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following protocol L, to the solution of 3-trifluoromethyl-5-isopropyl-pyrazole (0.22 g, 1.23 mmol) in CH3CN (10 mL) was added NCS (0.19 g, 1.43 mmol) in portions with vigorous stirring. The reaction mixture was then heated under reflux for 14 h, cooled and the reaction quenched with saturated NaHCO3, extracted with methylene chloride (2×30 mL) and the combined organic extracts was washed with brine, dried with Na2SO4 and evaporated to give the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder reflux for 14 h
  3. temperaturecooled
  4. customthe reaction quenched with saturated NaHCO3
  5. extractionextracted with methylene chloride (2×30 mL)
  6. washthe combined organic extracts was washed with brine
  7. dry with materialdried with Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-9366c7670978460d8299927a4adb9d2b
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Reaction notes

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