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

HRID 427664
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HRID 427664 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-30c617af48e04906b565b8add89d8fda
출처 데이터셋
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06313122B1

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