Hydrochloric Acid → HCID 178427873, compound

HRID 854131Notes

Reaction equation

HRID 854131 reaction equation
[CH:1]([NH:4][NH2:5])([CH3:3])[CH3:2].[F:6][C:7]([F:18])([F:17])[C:8](=O)[CH:9]([CH3:15])[C:10]([O:12]CC)=O.Cl>C(O)C>[OH:12][C:10]1[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[C:8]([C:7]([F:6])([F:17])[F:18])[C:9]=1[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 527891-IsopropylhydrazineHCID 2737204Ethyl 2-methyl-4,4,4-trifluoroacetoacetate

Product 1

HCID 178427873HCID 178427873, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7.4 g (100.0 mmol) of isopropylhydrazine in 100 ml of ethanol was added dropwise under stirring 23.3 g (purity: 85.0%, 100.0 mmol) of ethyl 4,4,4-trifluoro-2-methyl-3-oxobutanoate under ice-cooling so that the temperature in the reaction system did not exceed 10° C. After the dropwise addition, the whole was stirred at room temperature for 30 minutes. Then, 1 ml of concentrated hydrochloric acid was added into the reaction solution, followed by 2 days of stirring under refluxing. After the completion of the reaction was confirmed, the solvent was removed by evaporation under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate. The resulting organic layer was washed with water and saline, successively, and then dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure and the residue was washed with n-hexane to obtain 18.1 g (yield: 87.0%) of 5-hydroxy-4-methyl-1-iso-propyl-3-trifluoromethyl-1H-pyrazole as white crystals (melting point: 150 to 153° C.).

Workup

  1. temperaturecooling so that the temperature in the reaction system
  2. customdid not exceed 10° C
  3. additionAfter the dropwise addition
  4. waitfollowed by 2 days
  5. stirringof stirring
  6. temperatureunder refluxing
  7. customthe solvent was removed by evaporation under reduced pressure
  8. additionWater was added to the residue
  9. extractionfollowed by extraction with ethyl acetate
  10. washThe resulting organic layer was washed with water and saline
  11. dry with materialsuccessively, and then dried over anhydrous magnesium sulfate
  12. customThe solvent was removed by evaporation under reduced pressure
  13. washthe residue was washed with n-hexane

Sources & evidence

ORD record
ord-76cd84b99ee34e1eba8c43f23af6fa18
Source dataset
uspto-grants-2007_08
Patent number
US07256298B2

Reaction notes

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