Pyridine → [2-[[3,5-bis(trifluoromethyl)phenyl]carbamoyl]-4-chloro-phenyl] Acetate

HRID 2384389Notes

Reaction equation

HRID 2384389 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[OH:22])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.N1C=CC=CC=1.[C:32](Cl)(=[O:34])[CH3:33]>O1CCCC1>[C:32]([O:22][C:16]1[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=1[C:14]([NH:13][C:5]1[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:3]([C:2]([F:1])([F:24])[F:25])[CH:4]=1)=[O:23])(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 5081913Imd-0354

Product 1

HCID 9979865[2-[[3,5-bis(trifluoromethyl)phenyl]carbamoyl]-4-chloro-phenyl] AcetateYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[3,5-Bis(trifluoromethyl)phenyl]-5-chloro-2-hydroxybenzamide (1.51 g, 3 mmol) and pyridine (285 mg, 3.6 mmol) were dissolved in tetrahydrofuran (6 mL). Acetyl chloride (234 mg, 3.3 mmol) was added dropwise under ice cooling, and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure. 2 N hydrochloric acid was added to the residue, and it was extracted with ethyl acetate. After the ethyl acetate layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated, the residue was recrystallized from n-hexane-ethyl acetate to give the title compound (1.06 g, 83.0%) as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. addition2 N hydrochloric acid was added to the residue, and it
  3. extractionwas extracted with ethyl acetate
  4. washAfter the ethyl acetate layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customthe residue was recrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-090ec3acfc1a40f5a029ea32984c5ca1
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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