Acetic Acid → HCID 86684878, compound

HRID 238380Notes

Reaction equation

HRID 238380 reaction equation
C(O)(=O)C.[I:5]Cl.[CH3:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[CH:11][CH:10]=[N:9]1.C([O-])(=O)C.[Na+]>O>[I:5][C:11]1[CH:10]=[N:9][N:8]([CH3:7])[C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 72198667HCID 72198667, compound

Product 1

HCID 86684878HCID 86684878, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An acetic acid (3.3 mL) solution of iodine monochloride (2.64 g) was added dropwise to an acetic acid (22 mL) solution that contained 1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazole (3.70 g) and sodium acetate (1.38 g) at a room temperature, and the obtained solution was then stirred for 4 hours. Thereafter, water (250 mL) was added to the reaction solution, and the obtained solution was then stirred for 30 minutes. Then, a precipitated solid was collected by filtration, and was then washed with water. The obtained solid was dissolved in ethyl acetate, and the obtained solution was then washed with water and a saturated sodium hydrogencarbonate aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and was then concentrated under a reduced pressure. Thereafter, the residue was purified by column chromatography (silica gel 60N, hexane:ethyl acetate=5:1 to 7:3), so as to obtain the title compound (4.80 g) in the form of a brownish-red oily substance.

Workup

  1. customat a room temperature
  2. stirringthe obtained solution was then stirred for 30 minutes
  3. filtrationThen, a precipitated solid was collected by filtration
  4. washwas then washed with water
  5. dissolutionThe obtained solid was dissolved in ethyl acetate
  6. washthe obtained solution was then washed with water
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationwas then concentrated under a reduced pressure
  9. customThereafter, the residue was purified by column chromatography (silica gel 60N, hexane:ethyl acetate=5:1 to 7:3)

Sources & evidence

ORD record
ord-52781b8ce5ed4d33b1b49a19e6040326
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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