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

HRID 1387511

반응식

HRID 1387511 반응식
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].C(N(CC)CC)C>C(OCC)(=O)C>[N+:18]([C:12]1[CH:13]=[C:14]([NH:15][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:16]=[CH:17][C:11]=1[F:10])([O-:20])=[O:19]

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 8857Ethyl Acetate용매

실험 절차

Benzoyl chloride (12 mL, 103 mmol) was added dropwise to 4-fluoro-3-nitroaniline (15.64 g, 100 mmol) and triethylamine (17 mL, 122 mmol) in ethyl acetate (400 mL) at room temperature. The reaction mixture was stirred for 2 hours and then allowed to stand overnight. The reaction mixture was washed with 10% aqueous citric acid solution (200 mL) saturated aqueous sodium bicarbonate solution (200 mL), and brine (100 mL); dried (magnesium sulfate), filtered, and concentrated to about 100 mL at which point a solid began to precipitate. The mixture was cooled to zero degrees and the straw-colored solid collected by filtration to afford the product (21.1 g) in two crops.

후처리

  1. waitto stand overnight
  2. washThe reaction mixture was washed with 10% aqueous citric acid solution (200 mL) saturated aqueous sodium bicarbonate solution (200 mL), and brine (100 mL)
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated to about 100 mL at which point a solid
  6. customto precipitate
  7. temperatureThe mixture was cooled to zero degrees
  8. filtrationthe straw-colored solid collected by filtration

출처 및 근거

ORD 기록
ord-9ea7dc66c85f439f8b70aad45b55fe30
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06268387B1

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