Tetrahydrofuran → HCID 2740687, compound

HRID 1296472Notes

Reaction equation

HRID 1296472 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C1COCC1.[F:16][C:17]([F:35])([F:34])[C:18]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[N:20]([C:27]2[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=2)[N:19]=1.C(N(CC)CC)C>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:31][C:30]2[CH:29]=[CH:28][C:27]([N:20]3[C:21]([C:23]([F:24])([F:25])[F:26])=[CH:22][C:18]([C:17]([F:35])([F:34])[F:16])=[N:19]3)=[CH:33][CH:32]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 27406684-(3,5-Bis(trifluoromethyl)-1H-pyrazol-1-yl)aniline

Product 1

HCID 2740687HCID 2740687, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chlorobenzoyl chloride (88 mg) and THF (2 ml) were added to a mixture of 4-[3,5-bis(trifluoromethyl)-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-cb729eb9ff564c3db6cd3ac8933bce63
Source dataset
uspto-grants-2007_07
Patent number
US07247635B2

Reaction notes

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