Acetone → 1-Benzoyl-2-isopropylhydrazine

HRID 2250880Notes

Reaction equation

HRID 2250880 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:11][C:12]([CH3:14])=O.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>CCCCCC>[CH:12]([NH:10][NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:14])[CH3:11]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 11955BenzoylhydrazineHCID 12052Triethylsilane

Product 1

HCID 188691-Benzoyl-2-isopropylhydrazineYield 71.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of benzoylhydrazine (10 g, 73.45 mmol) in hexane (200 ml) was treated with acetone (54 mL, 734.5 mmol) and refluxed overnight. The precipitate was collected by suction filtration to afford a white solid which was treated with TFA (200 ml) and triethylsilane (24 mL, 149.24 mmol) at 60° C. overnight. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between DCM and 1N NaOH. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated to afford the product as a white solid (9.31 g, 71%).

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe precipitate was collected by suction filtration
  3. customto afford a white solid which
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customThe residue was partitioned between DCM and 1N NaOH
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a08399585b7c4b55ac77b1f86320325e
Source dataset
uspto-grants-2008_01
Patent number
US07317125B2

Reaction notes

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