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Phthalic Anhydride → 5-(Tert-butyldimethylsilyloxy)-2-phthalimido-1-nitrobenzene

HRID 395814
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 395814
[N+:1]([C:4]1[CH:10]=[C:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[C:19]1(=O)[O:24][C:22](=[O:23])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[Si:12]([O:11][C:9]1[CH:8]=[CH:7][C:5]([N:6]2[C:22](=[O:23])[C:21]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]3[C:19]2=[O:24])=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:14]
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Komponenten

5

Edukt 3

HCID 6811Phthalic AnhydrideHCID 81531DiisopropylethylamineHCID 120422994-(Tert-butyldimethylsilyl)oxy-2-nitroaniline

Produkt 1

HCID 181744725-(Tert-butyldimethylsilyloxy)-2-phthalimido-1-nitrobenzeneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2-nitro-4-(tert-butyldimethylsilyloxy)aniline (10.3 g, 38.5 mmol) and phthalic anhydride (6.50 g, 41.5 mmol) in toluene (30 mL) was refluxed for 18 h. A Dean-Stark apparatus was fitted to the flask, diisopropylethylamine (0.1 mL) was added and water was removed azeotropically over the next 24 h. About 20 mL of solvent was removed by distillation and the resultant solution allowed to cool to room temperature. The residue was diluted with methylene chloride and passed through a plug of silica gel eluting with methylene chloride. The desired fractions were combined and concentrated in vacuo. Recrystallization from methylene chloride-hexane provided 12.2 g (80%) of the title compound in two crops.

Aufarbeitung

  1. temperaturewas refluxed for 18 h
  2. additionwas added
  3. customwater was removed azeotropically over the next 24 h
  4. customAbout 20 mL of solvent was removed by distillation
  5. additionThe residue was diluted with methylene chloride
  6. concentrationconcentrated in vacuo
  7. customRecrystallization from methylene chloride-hexane

Quellen und Nachweise

ORD-Eintrag
ord-50aff6e8a9ad4efebff0cb77262d093c
Quelldatensatz
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06605626B2

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