StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Potassium Hydroxide → HCID 13935131, Verbindung

HRID 580714
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 580714
[OH-].[K+].[NH2:3][C:4]1[C:5]2[C:10]([N:11]=[C:12]3[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2.[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Br>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH:3][C:4]1[C:5]2[C:10]([N:11]=[C:12]3[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 680073-Fluorobenzyl bromideHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Produkt 1

HCID 13935131HCID 13935131, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysator
HCID 1140
Toluene
Lösungsmittel
2×

Versuchsvorschrift

In 300 ml of toluene and 200 ml of 30% potassium hydroxide were combined 8.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one and 1.92 g of tetrabutylammonium hydrogen sulfate catalyst. The mechanically stirred mixture was heated to reflux and a solution of 9.25 ml of 3-fluorobenzyl bromide in 40 ml of toluene was added over 0.5 hour. Then the reaction was further refluxed for 2 hours. The reaction mixture was then poured into 500 ml of ice and the layers were separated. The aqueous layer was extracted with ethyl acetate. The organics were combined and washed with saturated NaCl solution, dried over magnesium sulfate, filtered and evaporated to a solid. The solid was purified by preparative HPLC (ethyl acetate). The product-containing fractions were combined and concentrated to a solid. The solid was recrystallized from 1:1 dichloromethane/pentane to yield 7.15 g of solid, mp 156°-157° C.

Aufarbeitung

  1. temperatureThe mechanically stirred mixture was heated
  2. temperatureto reflux
  3. temperatureThen the reaction was further refluxed for 2 hours
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washwashed with saturated NaCl solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to a solid
  10. customThe solid was purified by preparative HPLC (ethyl acetate)
  11. concentrationconcentrated to a solid
  12. customThe solid was recrystallized from 1:1 dichloromethane/pentane

Quellen und Nachweise

ORD-Eintrag
ord-64d96ab27c294e0cb608c3bfe7964e05
Quelldatensatz
uspto-grants-1988_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04754050

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion