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Methanol → 2-[4-(4,5-Diphenylimidazol-1-yl)-butyl]-isoindol-1,3-dione

HRID 2251943
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2251943
[H-].[Na+].[C:3]1([C:9]2[N:10]=[CH:11][NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35].CO>CN(C=O)C>[C:3]1([C:9]2[N:10]=[CH:11][N:12]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]3[C:29](=[O:30])[C:28]4[C:27](=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:26]3=[O:35])[C:13]=2[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 695884,5-DiphenylimidazoleHCID 93575N-(4-Bromobutyl)phthalimide

Produkt 1

HCID 102239732-[4-(4,5-Diphenylimidazol-1-yl)-butyl]-isoindol-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

1.7 g (70.8 mmol) sodium hydride are placed in 130 ml DMF and 1.0 g (54.5 mmol) 4,5-diphenylimidazole are added under cooling. The suspension is stirred for four hours at RT and, subsequently, 15.4 g (54.5 mmol) N-(4-bromobutyl)-phthalimide dissolved in DMF is added dropwise under cooling. After complete addition, the reaction mixture is stirred for 12 hours at RT, 18 ml methanol are carefully added dropwise and the suspension is filtered. The filtrate is concentrated under vacuum and the residue is distributed between 500 ml chloroform and 170 ml water. The organic phase is dried over sodium sulfate and evaporated under vacuum until dry dried. The residue is purified by chromatography on silica gel with CHCl3/CH3OH (95/5) and subsequently crystallized from methanol: Yield 16.5 g (72%).

Aufarbeitung

  1. temperatureunder cooling
  2. additionis added dropwise
  3. temperatureunder cooling
  4. additionAfter complete addition
  5. stirringthe reaction mixture is stirred for 12 hours at RT
  6. filtrationthe suspension is filtered
  7. concentrationThe filtrate is concentrated under vacuum
  8. dry with materialThe organic phase is dried over sodium sulfate
  9. customevaporated under vacuum
  10. customuntil dry
  11. customdried
  12. customThe residue is purified by chromatography on silica gel with CHCl3/CH3OH (95/5)
  13. customsubsequently crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-ffbce5063ecf45bd848d1555cf4507b8
Quelldatensatz
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07320993B1

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