(4-Methylphenyl)hydrazine → 4,5-dihydro-1-(4-methylphenyl]-5-(4-methylsulphonylphenyl)-3-trifluoromethyl-1H-pyrazole

HRID 276141

Reaction equation

HRID 276141 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3](=O)/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][NH2:27])=[CH:22][CH:21]=1>C(O)C.Cl>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH:5]([C:6]3[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][CH:7]=3)[CH2:4][C:3]([C:2]([F:18])([F:17])[F:1])=[N:27]2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 10875(4-Methylphenyl)hydrazineHCID 15484796(E)-1,1,1-trifluoro-4-(4-methylsulphonylphenyl)-3-butene-2-one

Product 1

HCID 99298694,5-dihydro-1-(4-methylphenyl]-5-(4-methylsulphonylphenyl)-3-trifluoromethyl-1H-pyrazoleYield 32%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a flask with an inert atmosphere (E)-1,1,1-trifluoro-4-(4-methylsulphonylphenyl)-3-butene-2-one (prepared according to the method E-1) (1.83 g, 6.58 mmoles) and 4-methylphenylhydrazine chlorohydrate (1.04 g, 6.58 mmoles) are dissolved in 50 ml de ethanol. A few drops of hydrochloric acid are added, and the mixture refluxed under an inert atmosphere for 4 days. The mixture is cooled and the product crystallised. The solution is filtered and the product recrystallised from ethanol. 4,5-dihydro-1-(4-methylphenyl]-5-(4-methylsulphonylphenyl)-3-trifluoromethyl-1H-pyrazole (0.8 g, yield: 32%) is obtained in the form of a solid with a melting point of 140-3° C.

Workup

  1. temperaturethe mixture refluxed under an inert atmosphere for 4 days
  2. temperatureThe mixture is cooled
  3. customthe product crystallised
  4. filtrationThe solution is filtered
  5. customthe product recrystallised from ethanol

Sources & evidence

ORD record
ord-64c3958b6e4247e4815fd2db1550476b
Source dataset
uspto-grants-2002_03
Patent number
US06353117B1

Linked notes

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