Toluene → HCID 59515056, compound

HRID 1160053Notes

Reaction equation

HRID 1160053 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.C[O-].[Na+].C1(C)C=CC=CC=1.[C:21]1([C:27](=O)[CH:28]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:28]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 121574-Bromophenylhydrazine hydrochlorideHCID 34690551,2,3-triphenylpropane-1,3-dioneHCID 10942334Sodium Methoxide

Product 1

HCID 59515056HCID 59515056, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After this, 10.3 g (0.046 mole) of p-bromophenylhydrazine hydrochloride, 2.36 g (0.043 mole) of sodium methoxide, and 79.3 g of toluene were placed in a 300-ml four-necked flask. The mixture was then heated under reflux with stirring for three hours while distilling off methanol. To this reaction mixture was added 12.4 g (0.041 mole) of the 1,2,3-triphenylpropane-1,3-dione obtained above. After the addition, the mixture was heated under reflux with stirring for 20 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature and 39.7 g of water was added in drops. The reaction mixture was transferred to a separatory funnel and an organic layer was separated. The organic layer was concentrated under reduced pressure to dryness. The residue was purified by reslurrying with methanol and a solid was separated. To the solid was added 10.0 g of toluene in drops and the solid was dissolved by heating. To the resulting solution was added methanol in drops at 65° C. over a period of 30 minutes to effect precipitation. Thereafter, the mixture was cooled to room temperature and a solid was recovered by filtration. The solid was washed with methanol and dried under reduced pressure to give 10.2 g of 1-(p-bromophenyl)-3,4,5-triphenylpyrazole.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux
  3. distillationwhile distilling off methanol
  4. customobtained above
  5. additionAfter the addition
  6. temperaturethe mixture was heated
  7. temperatureunder reflux
  8. stirringwith stirring for 20 hours
  9. customUpon completion of the reaction
  10. customThe reaction mixture was transferred to a separatory funnel
  11. customan organic layer was separated
  12. concentrationThe organic layer was concentrated under reduced pressure to dryness
  13. customThe residue was purified
  14. customa solid was separated
  15. additionTo the solid was added 10.0 g of toluene in drops
  16. dissolutionthe solid was dissolved
  17. temperatureby heating
  18. additionTo the resulting solution was added methanol in drops at 65° C. over a period of 30 minutes
  19. customprecipitation
  20. temperatureThereafter, the mixture was cooled to room temperature
  21. filtrationa solid was recovered by filtration
  22. washThe solid was washed with methanol
  23. customdried under reduced pressure

Sources & evidence

ORD record
ord-5acf041e8454405caa208d2a6dd946cc
Source dataset
uspto-grants-2010_10
Patent number
US07816020B2

Reaction notes

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