Acetic Acid → 1H-Pyrazole, 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3,5-dimethyl-

HRID 1387709Notes

Reaction equation

HRID 1387709 reaction equation
[CH3:1][C:2](=O)[CH2:3][C:4](=O)[CH3:5].[Cl:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([Cl:19])[C:10]=1[NH:20][NH2:21].C(O)(=O)C>C(O)C>[Cl:8][C:9]1[CH:14]=[C:13]([C:15]([F:16])([F:18])[F:17])[CH:12]=[C:11]([Cl:19])[C:10]=1[N:20]1[C:4]([CH3:5])=[CH:3][C:2]([CH3:1])=[N:21]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31261AcetylacetoneHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine

Product 1

HCID 27410921H-Pyrazole, 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3,5-dimethyl-Yield 85.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pentan-2,4-dione (0.100 g) was added to a stirred solution of 2,6-dichloro-4-trifluoromethylphenylhydrazine (0.245 g) in ethanol (4.5 ml), followed by glacial acetic acid (0.5 ml), at room temperature. The reaction mixture was heated under reflux for 1 hour, then evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using dichloromethane as eluant, to provide a colourless oil initially which crystallised, after removal of extraneous solvent in vacuo, to furnish the title compound (0.265 g), m.p. 87-89° C. δ(CDCl3): 2.10 (s,3H), 2.32 (s,3H), 6.07 (s,1H), 7.72 (s,2H). MS (thermospray): M/Z [M] 309.0; C12H9Cl2F3N2 requires 309.12.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel
  5. customto provide a colourless oil initially which
  6. customcrystallised
  7. customafter removal of extraneous solvent in vacuo

Sources & evidence

ORD record
ord-29a28c6ca5b848f2b7d324c247f28e2b
Source dataset
uspto-grants-2001_07
Patent number
US06268509B1

Reaction notes

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