Diethyl Ether → N-(2-fluoro-5-nitrophenyl)benzamide

HRID 1357692

反応式

HRID 1357692 の反応式
C(N(CC)CC)C.[F:8][C:9]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:10]=1[NH2:11].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OCC)C>C(Cl)Cl>[CH3:23][CH2:22][CH2:21][CH:20]([CH3:25])[CH3:19].[F:8][C:9]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:10]=1[NH:11][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 677852-Fluoro-5-nitroaniline

生成物 2

HCID 78922-MethylpentaneHCID 675819N-(2-fluoro-5-nitrophenyl)benzamide収率 49%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Triethylamine (5.85 ml) was added to a an ice-cooled solution of 2-fluoro-5-nitroaniline (3.9 g) in dry methylene chloride under an argon atmosphere. Benzoyl chloride (4.18 ml) was added gradually. The resulting mixture was stirred at ambient temperature for 18 hours. The reaction mixture was partitioned between water and methylene chloride, the organic phase was washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate, filtered and evaporated to dryness to give a sticky solid. Trituration with hot isohexane and diethyl ether gave N-(2-fluoro-5-nitrophenyl)benzamide as a solid (3.2 g, 49%); NMR (CDCl3) 7.26 (dd, 1H), 7.6 (m, 3H), 7.91 (d, 2H), 8.03 (m, 1H), 8.15 (broad s, 1H), 9.48 (dd, 1H); m/s: M+H+ 261.

後処理

  1. customThe reaction mixture was partitioned between water and methylene chloride
  2. washthe organic phase was washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto give a sticky solid

出典と根拠

ORDレコード
ord-49c602cd1d9e4506b980a12d6d37334b
出典データセット
uspto-grants-2003_07
特許番号
US06593333B1

関連ノート

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