Water → 5-Chloro-2-pivaloyloxy-N-[3,5-bis(trifluoromethyl)phenyl]benzamide

HRID 1865350

Reaktionsgleichung

Reaktionsgleichung von HRID 1865350
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1)=[O:8].[H-].[Na+].[C:28](Cl)(=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30].O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:21])([F:22])[F:23])[CH:11]=1)=[O:8]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 62493Pivaloyl chlorideHCID 5081913Imd-0354

Produkt 1

HCID 98258505-Chloro-2-pivaloyloxy-N-[3,5-bis(trifluoromethyl)phenyl]benzamideAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 5-chloro-2-hydroxy-N-[3,5-bis(trifluoromethyl)phenyl]-benzamide(0.20 g, 0.52 mmol) in tetrahydrofuran(3 mL) was added to a suspension of 60% sodium hydride(21.8 mg, 0.55 mmol) in tetrahydrofuran (3 mL) under ice bath, and the mixture was stirred for 5 minutes. Then, pivaloyl chloride(71 μ L, 0.57 mmol) was added and the mixture was stirred for 10 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. After the ethyl acetate layer was washed successively with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was washed with isopropyl ether/n-hexane under suspension to give the title compound (195 mg, 80.2%) as a white crystal.

Aufarbeitung

  1. stirringthe mixture was stirred for 10 minutes
  2. extractionextracted with ethyl acetate
  3. washAfter the ethyl acetate layer was washed successively with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe residue obtained by evaporation of the solvent under reduced pressure
  6. washwas washed with isopropyl ether/n-hexane under suspension

Quellen und Nachweise

ORD-Eintrag
ord-f28626c45c48481298f5822048cbe5e1
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07626042B2

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