P-Toluenesulfonylhydrazide → HCID 12043829, compound

HRID 1280788Notes

Reaction equation

HRID 1280788 reaction equation
[CH:1](=[C:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([NH:27][NH2:28])(=O)=O)=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[C:2]1([C:1]2[C:8]3[CH2:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]=3[NH:27][N:28]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 15303P-ToluenesulfonylhydrazideHCID 2888762-Benzylidene-1-indanoneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 12043829HCID 12043829, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-benzylidene-indan-1-one (3.99 g), p-toluenesulphonyl hydrazine (4.0 g), p-toluenesulphonic acid hydrate (0.7 g) and ethanol (60 ml) was boiled under reflux for 1.5 hours and then left to stand for 18 hours at ambient temperature. The mixture was boiled under reflux for a further 74 hours and then left to stand at ambient temperature for 74 hours. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane (100 ml) and 2M sodium hydroxide solution (50 ml). The organic layer was separated, dried over magnesium sulfate and filtered. The magnesium sulfate was washed with ethyl acetate and filtered. The ethyl acetate filtrate was evaporated to dryness to give a solid which was recrystallized from ethanol to give 3-phenyl-1,4-dihydroindeno[1,2-c]pyrazole, m.p. 234-236° C.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. waitleft
  3. temperatureunder reflux for a further 74 hours
  4. waitleft
  5. waitto stand at ambient temperature for 74 hours
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was partitioned between dichloromethane (100 ml) and 2M sodium hydroxide solution (50 ml)
  8. customThe organic layer was separated
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. washThe magnesium sulfate was washed with ethyl acetate
  12. filtrationfiltered
  13. customThe ethyl acetate filtrate was evaporated to dryness
  14. customto give a solid which
  15. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-ff0088cdf05742fe8d7cfd37ad78c577
Source dataset
uspto-grants-2002_09
Patent number
US06451834B1

Reaction notes

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