Triethylamine → N-(4-iodophenyl)-2-nitroaniline

HRID 22491

反応式

HRID 22491 の反応式
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[I:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(OCC)(=O)C>[I:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 108934-IodoanilineHCID 738951-Fluoro-2-nitrobenzene

生成物 1

HCID 15045509N-(4-iodophenyl)-2-nitroaniline収率 48.2%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 2-fluoronitrobenzene (14 g, 100 mmol), 4-iodoaniline (11 g, 50 mmol) and triethylamine (14 ml, 100 mmol) was heated under reflux. After 48 h the reaction mixture was allowed to cool and ethyl acetate (300 ml) was added. The solution was washed with water (2×100 ml), aqueous 2M potassium hydroxide (100 ml) and brine (100 ml). The organics were dried over anhydrous magnesium sulphate and the solvent removed under reduced pressure to give an orange solid. Recrystalisation from ethyl acetate gave N-(4-iodophenyl)-2-nitroaniline (8.2 g, 48%) as an orange crystalline solid. deltaH (250 MHz, CDCl3) 9.39 (1H, s), 8.21 (1H, dd, J 8.5, 1.5 Hz), 7.71 (2H, dd, J 8.6, 2.0 Hz), 7.39 (1H, m), 7.24 (1H, m), 7.05 (2H, dd, J 8.6, 1.4 Hz), 6.83 (1H, m).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureto cool
  4. washThe solution was washed with water (2×100 ml), aqueous 2M potassium hydroxide (100 ml) and brine (100 ml)
  5. dry with materialThe organics were dried over anhydrous magnesium sulphate
  6. customthe solvent removed under reduced pressure
  7. customto give an orange solid
  8. customRecrystalisation from ethyl acetate

出典と根拠

ORDレコード
ord-01a5608ff8024c5eb682c47225811f55
出典データセット
uspto-grants-1995_06
特許番号
US05428168

関連ノート

読み込み中…