4-Fluoroaniline → HCID 10476762、化合物

HRID 2396042ノート

反応式

HRID 2396042 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH2:10][C:9](O[Si](C)(C)C)=[C:8](O[Si](C)(C)C)[CH2:7][C:6]=1[C:21]([O:23][CH3:24])=[O:22])=[O:4].[F:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:4])[C:5]1[C:6](=[CH:7][C:8]([NH:30][C:29]2[CH:31]=[CH:32][C:26]([F:25])=[CH:27][CH:28]=2)=[C:9]([NH:30][C:29]2[CH:31]=[CH:32][C:26]([F:25])=[CH:27][CH:28]=2)[CH:10]=1)[C:21]([O:23][CH3:24])=[O:22]

参加物

4

反応物 2

HCID 97314-FluoroanilineHCID 100221904,5-Bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester

生成物 1

HCID 10476762HCID 10476762、化合物

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of 2.4 g (6 mmol) of 4,5-bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (Example 1a) and 2.3 ml (24 mmol) of 4-fluoroaniline in 60 ml of glacial acetic acid is boiled under reflux for 2 hours. The reactionmixture is cooled, the solvent is evaporated off and the dark-brown residueis dissolved in dichloromethane and the solution is washed in succession with 20 ml of 1N HCl, 50 ml of saturated NaHCO3 and twice with 20 ml of water, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel with ethyl acetate/hexane 2:1 and the product fractions are concentrated by evaporation and recrystallized from ethyl acetate/hexane, yielding the title compound in the form of yellow crystals, 1H-NMR (CDCl3): δ=7.40 (s, 2H), 7.10-6.80 (m, 8H), 5.70 (br s2H), 3.83 (s, 6H).

後処理

  1. temperatureunder reflux for 2 hours
  2. temperatureThe reactionmixture is cooled
  3. customthe solvent is evaporated off
  4. dissolutionthe dark-brown residueis dissolved in dichloromethane
  5. washthe solution is washed in succession with 20 ml of 1N HCl, 50 ml of saturated NaHCO3 and twice with 20 ml of water
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated by evaporation
  8. customThe evaporation residue is chromatographed on silica gel with ethyl acetate/hexane 2:1
  9. concentrationthe product fractions are concentrated by evaporation
  10. customrecrystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-5f93890643e2492b88ad009763360b3d
出典データセット
uspto-grants-1996_02
特許番号
US05491144

反応ノート

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