Hydrochloric Acid → 3-(4-methoxy-2,5-dimethyl-phenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole

HRID 628529Notes

Reaction equation

HRID 628529 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[N:14](C)[N:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[C:5]([CH3:20])[CH:4]=1.Cl.O1CCC[CH2:23]1>>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[CH:11]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:13]([CH3:23])[N:14]=2)=[C:5]([CH3:20])[CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 1182364825-(4-methoxy-2,5-dimethyl-phenyl)-1-methyl-3-trifluoromethyl-1H-pyrazole

Product 1

HCID 1182364733-(4-methoxy-2,5-dimethyl-phenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole

Procedure

A mixture of 5-(4-methoxy-2,5-dimethyl-phenyl)-1-methyl-3-trifluoromethyl-1H-pyrazole (described in Reference preparation example 84) 3.2 g, 6N aqueous hydrochloric acid solution 5.3 ml and tetrahydrofuran 50 ml was stirred with heating under reflux for one hour. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium carbonate solution and saturated saline. The organic layer was dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 3-(4-methoxy-2,5-dimethyl-phenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole 3 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for one hour
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium carbonate solution and saturated saline
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-3623a6cfce774d0a8316a92214d59aa1
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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