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

HRID 22491

반응식

HRID 22491 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 15045509N-(4-iodophenyl)-2-nitroaniline수율 48.2%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-01a5608ff8024c5eb682c47225811f55
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428168

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