Tetrahydrofuran → HCID 2740687, compound

HRID 968322Notes

Reaction equation

HRID 968322 reaction equation
[Cl-].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C[O:12][CH2:11]C1.[F:14][C:15]([F:33])([F:32])[C:16]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[N:18]([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)[N:17]=1.C(N(CC)CC)C>O>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:11]([NH:29][C:28]2[CH:30]=[CH:31][C:25]([N:18]3[C:19]([C:21]([F:22])([F:23])[F:24])=[CH:20][C:16]([C:15]([F:14])([F:32])[F:33])=[N:17]3)=[CH:26][CH:27]=2)=[O:12])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 27406684-(3,5-Bis(trifluoromethyl)-1H-pyrazol-1-yl)anilineHCID 22288405HCID 22288405, compound

Product 1

HCID 2740687HCID 2740687, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chlorobenzol chloride (88 mg) and THF (2 ml) were added to a mixture of 4-[3,5-bis(trifluromethyl)-1H-pyrazol-1-yl]aniline (150 mg), triethylamine (57 mg) and THF (2 ml) under ice-cooling, followed by stirring at room temperature for 4 hours. Water was added to the reaction solution, the thus formed product was extracted with ethyl acetate and then the extract was washed with 1 N hydrochloric acid aqueous solution, saturated sodium bicarbonate aqueous solution and saturated brine in that order. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. By recrystallizing the resulting residue from a mixed solvent of ethyl acetate and n-hexane, 4-chloro-4′-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]benzanilide (105 mg) was obtained as colorless powder crystals.

Workup

  1. temperaturecooling
  2. extractionthe thus formed product was extracted with ethyl acetate
  3. washthe extract was washed with 1 N hydrochloric acid aqueous solution, saturated sodium bicarbonate aqueous solution and saturated brine in that order
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customBy recrystallizing the resulting residue from a mixed solvent of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-0f314022335a4f229713814ef3f4a440
Source dataset
uspto-grants-2005_10
Patent number
US06958339B2

Reaction notes

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