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

HRID 1865350

반응식

HRID 1865350 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 98258505-Chloro-2-pivaloyloxy-N-[3,5-bis(trifluoromethyl)phenyl]benzamide수율 80.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f28626c45c48481298f5822048cbe5e1
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07626042B2

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