2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → 5-Amino-4-ethoxycarbonyl-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)-pyrazole
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:17]([C:19](=[CH:25]OCC)[C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:18].C(OCC)C.CCCCC>C(O)C>[NH2:18][C:17]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:25][C:19]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 15.7 grams (0.634 mole) of 2,3,5,6-tetrafluoro-4-trifluoromethylphenylhydrazine in 40 mL of anhydrous ethanol was added 10.7 grams (0.634 mole) of ethyl 2-cyano-3-ethoxyacrylate. The reaction mixture was heated at reflux for 21 hours, then cooled, and the solvent was removed by distillation under reduced pressure, leaving a residue. This residue was suspended in 80 mL of a 50:50 mixture of diethyl ether/n-pentane. A solid formed and was removed by filtration to yield 20.4 grams of ethyl 5-amino-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazol-4-ylcarboxylate, m.p. 166-168° C. The nmr spectrum was consistent with the proposed structure.
Workup
- temperatureThe reaction mixture was heated
- temperatureat reflux for 21 hours
- temperaturecooled
- customthe solvent was removed by distillation under reduced pressure
- customleaving a residue
- customA solid formed
- customwas removed by filtration
Sources & evidence
- ORD record
- ord-81f4c52acd6642549952368dcad2ac8d
- Source dataset
- uspto-grants-1992_12
- Patent number
- US05167691
Reaction notes
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