Tetrahydrofuran → HCID 178493574, compound

HRID 2404566Notes

Reaction equation

HRID 2404566 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](Cl)(=[O:22])[CH2:18][C:19](Cl)=[O:20].O1CCC[CH2:25]1>>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][CH2:10][C:11]([F:13])([F:14])[F:12])=[CH:4][C:3]=1[N:15]1[C:19]([OH:20])=[CH:18][C:17]([O:22][CH3:25])=[N:16]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 74269Propanedioyl dichlorideHCID 66842008HCID 66842008, compound

Product 1

HCID 178493574HCID 178493574, compound

Procedure

1.5 g of 2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenylhydrazine was dissolved in 70 mL of tetrahydrofuran, and 0.83 g of malonyl chloride was added under cooling with ice. Stirring was carried out under reflux with heating for 5 hours, and the solvent was distilled off under reduced pressure. To the obtained residue, 20 mL of dichloromethane and 2 mL of methanol were added, and 0.7 mL of a diethyl ether solution (2.0 mol/L) of trimethylsilyldiazomethane was added under cooling with ice, followed by stirring at room temperature for 5 hours. Then, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:1) to obtain 0.14 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-5-hydroxy-3-methoxypyrazole.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder reflux
  3. temperaturewith heating for 5 hours
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionTo the obtained residue, 20 mL of dichloromethane and 2 mL of methanol were added
  6. addition0.7 mL of a diethyl ether solution (2.0 mol/L) of trimethylsilyldiazomethane was added
  7. temperatureunder cooling with ice
  8. stirringby stirring at room temperature for 5 hours
  9. distillationThen, the solvent was distilled off under reduced pressure
  10. customthe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-8f03ea9d8dfb495ca4bc3c2c37f73996
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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