Acetone → 1-Benzoyl-2-isopropylhydrazine

HRID 1724120Notes

Reaction equation

HRID 1724120 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-fd359c6bc45b44dea6117b909e884033
Source dataset
uspto-grants-2009_02
Patent number
US07485752B2

Reaction notes

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