Benzoyl chloride → N-(4-fluoro-3-nitrophenyl)benzamide

HRID 605225

반응식

HRID 605225 반응식
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CCN(CC)CC.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 677684-Fluoro-3-nitroaniline

생성물 1

HCID 3535228N-(4-fluoro-3-nitrophenyl)benzamide수율 81.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
5 °C

실험 절차

To a solution of 4-fluoro-3-nitroaniline (2.00 g, 12.8 mmol) and Et3N (1.98 mL, 14.1 mmol) in THF (40 mL) was added benzoyl chloride (1.58 ml, 13.5 mmol) dropwise at 5° C. The mixture was stirred at 5° C. for 1 hour, warmed to room temperature, and then evaporated. The residue was suspended in H2O (100 ml), adjusted to pH 2, and then extracted with EtOAc. The extract was washed with H2O, 10% NaHCO3 and brine, dried over MgSO4, and concentrated under vacuum to give the crude product, which was purified by washing with i-Pr2O to give the title compound as pale brown crystal (2.70 g, 81%).

후처리

  1. temperaturewarmed to room temperature
  2. customevaporated
  3. extractionextracted with EtOAc
  4. washThe extract was washed with H2O, 10% NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum
  7. customto give the crude product, which
  8. customwas purified
  9. washby washing with i-Pr2O

출처 및 근거

ORD 기록
ord-fc9411b66fab42c6a4fae27770980d1c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910595B2

연결된 노트

불러오는 중…