2-Iodoaniline → HCID 21753017, Verbindung

HRID 2396053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2396053
[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].[I:25][C:26]1[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=1[NH2:28]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:4])[C:5]1[C:6](=[CH:7][C:8]([NH:28][C:27]2[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=2[I:25])=[C:9]([NH:28][C:27]2[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=2[I:25])[CH:10]=1)[C:21]([O:23][CH3:24])=[O:22]

Komponenten

4

Edukt 2

HCID 119952-IodoanilineHCID 100221904,5-Bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester

Produkt 1

HCID 21753017HCID 21753017, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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 5.3 g (24 mmol) of 2-iodoaniline 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 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 residue obtained after concentration by evaporation is chromatographed on silica gel with ethyl acetate/hexane 2:1 and the product fractions are concentrated by evaporation, yielding the title compound in the form of a yellow foam: 1H-NMR (DMSO-d6): δ=7.91 (dxd, J1 =8, J2 =1, 2H), 7.39 (dxdxd, J1 =10, J2 =8, J3 =1, 2H), 7.32 (br s, 2H), 7.22-7.05 (m, 2H), 7.01 (s, 2H), 6.88 (txd, Jt =8, Jd =1, 2H), 3.73 (s, 6H).

Aufarbeitung

  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 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 residue obtained
  9. concentrationafter concentration
  10. customby evaporation
  11. customis chromatographed on silica gel with ethyl acetate/hexane 2:1
  12. concentrationthe product fractions are concentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-2c6ce8c10c0246b5a258d204f7604e4f
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05491144

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