2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → HCID 14421338, compound

HRID 2107881Notes

Reaction equation

HRID 2107881 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([F:12])[C:3]=1[NH:13][NH2:14].C(O[CH:18]=[C:19]([C:25]#[N:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])C>C(O)C>[NH2:26][C:25]1[N:13]([C:3]2[C:4]([F:12])=[CH:5][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:7][C:2]=2[Cl:1])[N:14]=[CH:18][C:19]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 2

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 13913421[2-Chloro-6-fluoro-4-(trifluoromethyl)phenyl]hydrazine

Product 1

HCID 14421338HCID 14421338, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

200 g (0.88 mol) of 2-chloro-6-fluoro-4-trifluoromethylphenylhydrazine and 151 g (0.88 mol) of ethyl ethoxymethylenecyanoacetate in 400 ml of ethanol are heated to the reflux temperature for 30 hours, the mixture is then concentrated to approximately half of the volume and cooled and the precipitate thus obtained is filtered off, washed with a little cold ethanol and dried. 250 g (81% of theory) of ethyl 5-amino-1-(2-chloro-6-fluoro-4-trifluoromethylphenyl)-pyrazol-4-yl carboxylate of melting point 147°-149° C. are obtained.

Workup

  1. concentrationthe mixture is then concentrated to approximately half of the volume
  2. temperaturecooled
  3. customthe precipitate thus obtained
  4. filtrationis filtered off
  5. washwashed with a little cold ethanol
  6. customdried

Sources & evidence

ORD record
ord-48a05952f57e4657a89bf06f728a089e
Source dataset
uspto-grants-1990_06
Patent number
US04936892

Reaction notes

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