2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → 5-Amino-4-ethoxycarbonyl-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)-pyrazole

HRID 2232175Notes

Reaction equation

HRID 2232175 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([C:9]([F:12])([F:11])[F:10])[C:5]([F:13])=[C:4]([F:14])[C:3]=1[NH:15][NH2:16].C(O[CH:20]=[C:21]([C:27]#[N:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])C>C(O)C>[NH2:28][C:27]1[N:15]([C:3]2[C:2]([F:1])=[C:7]([F:8])[C:6]([C:9]([F:12])([F:11])[F:10])=[C:5]([F:13])[C:4]=2[F:14])[N:16]=[CH:20][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

4

Reactant 2

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 298179(alpha,alpha,alpha,2,3,5,6-Heptafluoro-p-tolyl)hydrazine

Product 1

HCID 139337085-Amino-4-ethoxycarbonyl-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)-pyrazoleYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

40 g (0.161 mol) of 2,3,5,6-tetrafluoro-4-trifluoromethylphenylhydrazine and 27.8 g (0.161 mol) of ethyl ethoxymethylenecyanoacetate are dissolved in 70 ml of ethanol and the solution is warmed under reflux for 10 hours. The solvent is distilled off in vacuo, the residue is suspended in 100 ml of diethyl ether, the suspension is filtered and the solid is dried. 52.2 g (87.4% of theory) of 5-amino-4-ethoxycarbonyl-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)-pyrazole of melting point 175° C.-176° C. are obtained.

Workup

  1. temperaturethe solution is warmed
  2. temperatureunder reflux for 10 hours
  3. distillationThe solvent is distilled off in vacuo
  4. filtrationthe suspension is filtered
  5. customthe solid is dried

Sources & evidence

ORD record
ord-6a2863a51dcf42b8814ae7265b38d15a
Source dataset
uspto-grants-1988_11
Patent number
US04787930

Reaction notes

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