Aniline → dimethyl 4,5-dianilinobenzene-1,2-dicarboxylate

HRID 1376751ノート

反応式

HRID 1376751 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].[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[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:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:9]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:10]=1)[C:21]([O:23][CH3:24])=[O:22]

参加物

4

反応物 2

HCID 6115AnilineHCID 100221904,5-Bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester

生成物 1

HCID 10407176dimethyl 4,5-dianilinobenzene-1,2-dicarboxylate

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of 5.6 g (15 mmol) of 4,5-bis(trimethylsilyloxy)cyclohexa 1,4-diene- 1,2-dicarboxylic acid dimethyl ester and 5.5 ml (60 mmol) of aniline in 60 ml of glacial acetic acid is boiled under reflux for 4 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 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 crude product is recrystallized from ethanol, yielding the title compound in the form of yellow crystals, m.p. 178°, FAB-MS: 377 [M+ +H].

後処理

  1. temperatureunder reflux for 4 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 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 crude product is recrystallized from ethanol

出典と根拠

ORDレコード
ord-0975828cec7e4e3b9f447a3e21c207d3
出典データセット
uspto-grants-1997_09
特許番号
US05663336

反応ノート

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