HCID 59448818, compound → HCID 68485221, compound

HRID 2404576Notes

Reaction equation

HRID 2404576 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[NH:15][NH2:16].[C:17]([C:19](=[C:25]([O:29]CC)[O:26][CH2:27][CH3:28])[C:20]([O:22][CH2:23][CH3:24])=O)#[N:18]>C(O)C>[CH2:27]([O:26][C:25]([C:19]1[C:20]([O:22][CH2:23][CH3:24])=[N:16][N:15]([C:3]2[CH:4]=[C:5]([S:9][CH2:10][C:11]([F:13])([F:14])[F:12])[C:6]([CH3:8])=[CH:7][C:2]=2[F:1])[C:17]=1[NH2:18])=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 59448818HCID 59448818, compoundHCID 66842008HCID 66842008, compound

Product 1

HCID 68485221HCID 68485221, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.0 g of 2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenylhydrazine was dissolved in 50 mL of ethanol, and 5.0 g of ethyl 2-cyano-3,3-diethoxyacrylate was added, followed by stirring under reflux with heating for 6 hours. Then, the solvent was distilled off under reduced pressure, and extraction with ethyl acetate was carried out. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:3) to obtain 1.48g of ethyl-5-amino-3-ethoxy-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}pyrazole-4-carboxylate.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 6 hours
  3. distillationThen, the solvent was distilled off under reduced pressure, and extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-01f82a2f428743bfb0499160f37ce6c8
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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