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

HRID 1376751노트

반응식

HRID 1376751 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-0975828cec7e4e3b9f447a3e21c207d3
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05663336

반응 노트

불러오는 중…