Hydrochloric Acid → N-[3,5-Bis(trifluoromethyl)phenyl]-5-ethynyl-2-hydroxybenzamide

HRID 421054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 421054
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:28])[C:15]2[CH:20]=[C:19]([C:21]#[C:22][Si](C)(C)C)[CH:18]=[CH:17][C:16]=2[OH:27])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]([F:29])([F:30])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:28])[C:15]2[CH:20]=[C:19]([C:21]#[CH:22])[CH:18]=[CH:17][C:16]=2[OH:27])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10343463N-[3,5-Bis(trifluoromethyl)phenyl]-2-hydroxy-5-[(trimethylsilyl)ethynyl]benzamide

Produkt 1

HCID 11773173N-[3,5-Bis(trifluoromethyl)phenyl]-5-ethynyl-2-hydroxybenzamideAusbeute 35,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

N-[3,5-Bis(trifluoromethyl)phenyl]-2-hydroxy-5-[(trimethylsilyl)ethynyl]benzamide (233 mg, 0.5 mmol) was dissolved in methanol (1 mL). 2 N sodium hydroxide (1 mL) was added, 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 crystallized from ethanol-water to give the title compound (67 mg, 35.9%) as a light gray crystal.

Aufarbeitung

  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. customThe obtained residue was crystallized from ethanol-water

Quellen und Nachweise

ORD-Eintrag
ord-dd96188744524987ad3aa14ed86abe48
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097759B2

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