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

HRID 619310Notes

Reaction equation

HRID 619310 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-54b7b220d6dc46f79a576704db35c0e6
Source dataset
uspto-grants-1999_09
Patent number
US05958948

Reaction notes

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