Hydrochloric Acid → HCID 9975091, compound

HRID 421012Notes

Reaction equation

HRID 421012 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[F:9][C:10]([F:25])([F:24])[C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1)[C:14](Cl)=[O:15].Cl.[OH-].[Na+]>ClCCl.N1C=CC=CC=1>[F:9][C:10]([F:24])([F:25])[C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([C:20]([F:23])([F:21])[F:22])[CH:19]=1)[C:14]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 58012-AminophenolHCID 14798Sodium HydroxideHCID 1018563,5-Bis(trifluoromethyl)benzoyl chloride

Product 1

HCID 9975091HCID 9975091, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-Aminophenol (120 mg, 1.1 mmol) was dissolved in dichloromethane (5 mL). A solution of 3,5-bis(trifluoromethyl)benzoyl chloride (300 mg, 1.1 mmol) in dichloromethane (3 mL) and pyridine (0.5 mL) was added dropwise under ice cooling and argon atmosphere, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 2 N hydrochloric acid and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and brine one after another, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was dissolved in ethanol (5 mL), added dropwise 2 N sodium hydroxide (0.1 mL, 0.2 mmol), and stirred at room temperature for 30 minutes. The reaction mixture was poured into 2 N hydrochloric acid and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and brine one after another, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give the title compound (288 mg, 73.6%) as a light pink crystal.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the ethyl acetate layer was washed with water and brine one after another,
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in ethanol (5 mL)
  6. stirringstirred at room temperature for 30 minutes
  7. extractionextracted with ethyl acetate
  8. washAfter the ethyl acetate layer was washed with water and brine one after another,
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c8e78f2bd1fe49a3bcda831da381078f
Source dataset
uspto-grants-2012_01
Patent number
US08097759B2

Reaction notes

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