Thionyl Chloride → HCID 86629852, compound

HRID 1952258Notes

Reaction equation

HRID 1952258 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8](O)=[O:9])[C:4]([C:11]([F:14])([F:13])[F:12])=[N:3]1.S(Cl)([Cl:17])=O>>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([Cl:17])=[O:9])[C:4]([C:11]([F:14])([F:13])[F:12])=[N:3]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 19754695HCID 19754695, compound

Product 1

HCID 86629852HCID 86629852, compound

Procedure

1,5-Dimethyl-3-trifluoromethylpyrazole-4-carboxylic acid (2.09 g, 10 mmol) was dissolved in thionyl chloride, and the mixture was heated under reflux for 3 hr. The mixture was concentrated under reduced pressure to give 1,5-dimethyl-3-trifluoromethylpyrazole-4-carbonyl chloride. This was added to a solution of 3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline (3.29 g, 10 mmol) and triethylamine (3.03 g, 30 mmol) in tetrahydrofuran (30 ml), and the mixture was heated under reflux for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with water, and dried over magnesium sulfate. After concentration under reduced pressure, the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired compound (3.64 g) as crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-88f077316add41dfaa1956c259991e53
Source dataset
uspto-grants-2013_03
Patent number
US08404861B2

Reaction notes

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