Hydrochloric Acid → HCID 58345409, compound

HRID 1877976Notes

Reaction equation

HRID 1877976 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]([N:10]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)=[CH:13][C:12]([C:25]([O:27]CC)=[O:26])=[N:11]2)[CH:7]=[CH:8][CH:9]=1.Cl>CO.O>[Cl:3][C:4]1[CH:5]=[C:6]([N:10]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)=[CH:13][C:12]([C:25]([OH:27])=[O:26])=[N:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58345406HCID 58345406, compound

Product 1

HCID 58345409HCID 58345409, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

8.5 g (152 mmol) of potassium hydroxide are added to a solution of 6 g (15.2 mmol) of ethyl 1-(3-chlorophenyl)-5-[3-(trifluoromethyl)phenyl]-1H-pyrazole-3-carboxylate from example 4A in 80 ml of methanol and the mixture is stirred for 30 minutes under reflux. The reaction mixture is diluted with water and rendered acidic using 1 molar hydrochloric acid. The mixture is extracted with ethyl acetate. The organic phase is washed with a sodium chloride solution, dried over sodium sulfate and concentrated on a rotary evaporator. The residue obtained is crystallized from diethyl ether/pentane. The crystals are collected by suction filtration, washed with a little pentane and dried. 5.2 g (14.2 mmol, 93% yield of theory) of product are obtained.

Workup

  1. temperatureunder reflux
  2. extractionThe mixture is extracted with ethyl acetate
  3. washThe organic phase is washed with a sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue obtained
  7. customis crystallized from diethyl ether/pentane
  8. filtrationThe crystals are collected by suction filtration
  9. washwashed with a little pentane
  10. customdried
  11. custom5.2 g (14.2 mmol, 93% yield of theory) of product are obtained

Sources & evidence

ORD record
ord-19295045f2a247b787323d0b3793842e
Source dataset
uspto-grants-2012_11
Patent number
US08314089B2

Reaction notes

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