Hydrochloric Acid → HCID 178427863, compound

HRID 2404568Notes

Reaction equation

HRID 2404568 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(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][C:26](Cl)=[O:27].Cl>O1CCCC1.O>[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[CH:24]=[CH:25][C:26]([OH:27])=[N:16]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 84944Propanoyl chloride, 3-bromo-HCID 66842008HCID 66842008, compound

Product 1

HCID 178427863HCID 178427863, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

12 g of 2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenylhydrazine was dissolved in 200 mL of tetrahydrofuran, and 100 mL of water was added. To this solution, 16 g of potassium carbonate and 8.1 g of 3-bromopropionyl chloride were added, followed by stirring at room temperature for 5 hours. The aqueous layer was neutralized to the vicinity of pH 2 with 6N hydrochloric acid. Then, the solvent was distilled off under reduced pressure, and the residue was subjected to extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a solid, which was washed with hexane. Then, this solid was dissolved in 200 mL of toluene, and 100mL of water was added. Then, 3.7 g of potassium permanganate and tetra n-butyl ammonium bromide in a catalytic amount were added, followed by stirring at room temperature for 10 minutes. Then, an insoluble solid was removed by filtration, and the organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the solid was washed with hexane to obtain 8.7 g of pale yellow crystals (melting point: 166-168° C.).

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. extractionthe residue was subjected to extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto obtain a solid, which
  6. washwas washed with hexane
  7. dissolutionThen, this solid was dissolved in 200 mL of toluene
  8. addition100mL of water was added
  9. additionThen, 3.7 g of potassium permanganate and tetra n-butyl ammonium bromide in a catalytic amount were added
  10. stirringby stirring at room temperature for 10 minutes
  11. customThen, an insoluble solid was removed by filtration
  12. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  13. distillationThen, the solvent was distilled off under reduced pressure
  14. washthe solid was washed with hexane

Sources & evidence

ORD record
ord-597c0c6972fd490f93da2608e184fe64
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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