Triethylamine → 2-(2,4-Dinitrophenoxy)-1H-isoindole-1,3(2H)-dione

HRID 876811

Reaktionsgleichung

Reaktionsgleichung von HRID 876811
[OH:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].CCN(CC)CC.Br[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=1[N+:30]([O-:32])=[O:31]>CC(C)=O>[N+:27]([C:24]1[CH:23]=[C:22]([N+:30]([O-:32])=[O:31])[CH:21]=[CH:26][C:25]=1[O:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12])([O-:29])=[O:28]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 114411-Bromo-2,4-dinitrobenzene

Produkt 1

HCID 70363092-(2,4-Dinitrophenoxy)-1H-isoindole-1,3(2H)-dioneAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a suspension of 2-hydroxyisoindoline-1,3-dione (20.0 g, 0.12 mol) in acetone (400 mL) was added Et3N (14.9 g, 0.15 mol), the mixture was stirred at room temperature until it became a homogeneous solution, then 1-bromo-2,4-dinitrobenzene Y-1 (30.2 g, 0.12 mol) was added. The reaction was stirred at room temperature for 3 h, then poured into ice-water, the resulting precipitate was filtered and washed three times with cold MeOH, dried in vacuum to afford the title compound (38.1 g).

Aufarbeitung

  1. stirringThe reaction was stirred at room temperature for 3 h
  2. filtrationthe resulting precipitate was filtered
  3. washwashed three times with cold MeOH
  4. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-dbb3f970c0724ff3a7a479fecd60add1
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987269B2

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