P-Toluenesulfonylhydrazide → HCID 19872068, compound

HRID 329408Notes

Reaction equation

HRID 329408 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=O)[CH3:13])=[CH:8][CH:7]=1.[S:15]([NH:25][NH2:26])(C1C=CC(C)=CC=1)(=O)=O.S(Cl)(Cl)=O>C(O)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:26]=[N:25][S:15][CH:13]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 15303P-ToluenesulfonylhydrazideHCID 24386Thionyl ChlorideHCID 223197741-[4-(4-Chlorobutyl)phenyl]ethan-1-one

Product 1

HCID 19872068HCID 19872068, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 125 ml round-bottomed flask equipped with condenser and N2 inlet were added 6.25 g (29.65 mmol) p-(4-chlorobutyl)acetophenone, 5.57 g (29.65 mmol) tosylhydrazine, and 50 ml ethanol. The reaction was refluxed 3.5 hours, cooled, and evaporated. The residue was taken up in 23.4 ml (326 mmol) thionyl chloride and stirred at room temperature for 3 hours. The reaction mixture was evaporated and the residue chromatographed on silica gel using hexane/methylene chloride as eluent to afford an oil, 6.1 g (81.5%). NMR (CDCl3): 1.84 (m, 4H), 2.73 (m, 2H), 3.58 (m, 2H), 7.3 and 7.95 (m, 4H), 8.59 (s, 1H).

Workup

  1. customTo a 125 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 3.5 hours
  3. temperaturecooled
  4. customevaporated
  5. customThe reaction mixture was evaporated
  6. customthe residue chromatographed on silica gel
  7. customto afford an oil, 6.1 g (81.5%)

Sources & evidence

ORD record
ord-84060594417c47769905236c51b022fe
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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