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

HRID 1387511

反応式

HRID 1387511 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9ea7dc66c85f439f8b70aad45b55fe30
出典データセット
uspto-grants-2001_07
特許番号
US06268387B1

関連ノート

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