Potassium Hydroxide → HCID 13935142, Verbindung

HRID 580719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 580719
[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]([F:30])([F:29])[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Br>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:19][C:20]([F:29])([F:30])[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][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

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Produkt 1

HCID 13935142HCID 13935142, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

In 150 ml of toluene and 700 ml of 30% potassium hydroxide were combined 3.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one and 0.72 g of tetrabutylammonium hydrogen sulfate. The reaction was mechanically stirred and heated with a steam bath. To it was added dropwise a solution of 13.5 g 3-trifluoromethylbenzyl bromide in 30 ml of toluene over 1 hour. After the addition, heating was continued 1 hour during which the reaction went to completion. The organic phase was separated, washed with ice-cold saturated NaCl solution, dried over anhydrous magnesium sulfate, filtered and evaporated to an oil. The oil was diluted with 10 ml of ethyl acetate and purified by preparative HPLC (ethyl acetate). The product-containing fractions were evaporated and recrystallized from DCM/hexane to yield 2.20 g of solid, mp 147°-149° C.

Aufarbeitung

  1. temperatureheated with a steam bath
  2. additionAfter the addition
  3. temperatureheating
  4. customThe organic phase was separated
  5. washwashed with ice-cold saturated NaCl solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to an oil
  9. additionThe oil was diluted with 10 ml of ethyl acetate
  10. custompurified by preparative HPLC (ethyl acetate)
  11. customThe product-containing fractions were evaporated
  12. customrecrystallized from DCM/hexane

Quellen und Nachweise

ORD-Eintrag
ord-13702dbeaeb74a738c780bc48513ead8
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04754050

Notizen zur Reaktion

Wird geladen…