N,N-Diethyl-p-phenylenediamine → HCID 10346545、化合物

HRID 2396048ノート

反応式

HRID 2396048 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].[CH2:25]([N:27]([C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)[CH2:28][CH3:29])[CH3:26]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:4])[C:5]1[C:6](=[CH:7][C:8]([NH:34][C:33]2[CH:32]=[CH:31][C:30]([N:27]([CH2:28][CH3:29])[CH2:25][CH3:26])=[CH:36][CH:35]=2)=[C:9]([NH:34][C:33]2[CH:32]=[CH:31][C:30]([N:27]([CH2:28][CH3:29])[CH2:25][CH3:26])=[CH:36][CH:35]=2)[CH:10]=1)[C:21]([O:23][CH3:24])=[O:22]

参加物

4

反応物 2

HCID 7120N,N-Diethyl-p-phenylenediamineHCID 100221904,5-Bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester

生成物 1

HCID 10346545HCID 10346545、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 3.94 g (24 mmol) of 4-(N,N-diethyl-amino)-aniline in 24 ml of glacial acetic acid is boiled under reflux for 2 hours. The reaction mixture is cooled, the solvent is evaporated off and the dark-brown residue is dissolved in dichloromethane and the solution is washed in succession with 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 onsilica gel with dichloromethane/methanol 400:15 and the product fractions are concentrated by evaporation and again chromatographed on silica gel with ethyl acetate/hexane 1:1. The product fractions are concentrated by evaporation, yielding the title compound in the form of green crystals, FAB-MS: 518 [M+ ], 519 [M+ +H].

後処理

  1. temperatureunder reflux for 2 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent is evaporated off
  4. dissolutionthe dark-brown residue is dissolved in dichloromethane
  5. washthe solution is washed in succession with 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 onsilica gel with dichloromethane/methanol 400:15
  9. concentrationthe product fractions are concentrated by evaporation
  10. customagain chromatographed on silica gel with ethyl acetate/hexane 1:1
  11. concentrationThe product fractions are concentrated by evaporation

出典と根拠

ORDレコード
ord-762a6479de0642b6b1fd1ab1811c0429
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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