[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine → Methyl 1-(2,6-dichloro-4-trifluoromethylphenyl)-3,5-diethylpyrazole4-carboxylate

HRID 725271Notes

Reaction equation

HRID 725271 reaction equation
[CH3:1][O:2][C:3]([CH:5]([C:10](=O)[CH2:11][CH3:12])[C:6](=O)[CH2:7][CH3:8])=[O:4].[Cl:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([Cl:25])[C:16]=1[NH:26][NH2:27]>C(O)C>[Cl:14][C:15]1[CH:20]=[C:19]([C:21]([F:23])([F:22])[F:24])[CH:18]=[C:17]([Cl:25])[C:16]=1[N:26]1[C:10]([CH2:11][CH3:12])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:6]([CH2:7][CH3:8])=[N:27]1

Participants

4

Reactant 2

HCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 21837307Methyl 3-oxo-2-propionylpentanoate

Product 1

HCID 21837355Methyl 1-(2,6-dichloro-4-trifluoromethylphenyl)-3,5-diethylpyrazole4-carboxylateYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7.5 g (40 mmol) of the compound of step A and 11.85 g (48 mmol) of 2,6-dichloro-4-trifluoromethylphenyl hydrazine in 50 mL of ethanol was heated at reflux for 8 hours. The ethanol was removed by evaporation and the residues were partitioned between ethyl acetate and dilute hydrogen chloride. The organic extracts were dried and evaporated to give the desired product in 43% yield as a maroon oil. 1H-NMR (CDCl3) δ1.08 (3H, t, J=7), 1.24 (3H, t, J=7), 2.22 (2H, q, J=7), 2.94 (2H, q, J=7), 3.86 (3H, s), 7.46 (2H, s).

Workup

  1. temperatureat reflux for 8 hours
  2. customThe ethanol was removed by evaporation
  3. customthe residues were partitioned between ethyl acetate and dilute hydrogen chloride
  4. customThe organic extracts were dried
  5. customevaporated

Sources & evidence

ORD record
ord-e91aee26bee54c378d88f9cff6780018
Source dataset
uspto-grants-1998_01
Patent number
US05705646

Reaction notes

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