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

2-Chloro-4,6-diphenyl-1,3,5-triazine → 6-(4,6-Diphenyl-1,3,5-triazin-2-yl)-8,8-dimethyl-8H-indolo[3,2,1-de]acridine

HRID 1627748
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1627748
[CH3:1][C:2]1([CH3:25])[C:15]2[C:10]3=[C:11]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[N:9]3[C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=3)[CH:12]=[C:13](B(O)O)[CH:14]=2.Cl[C:27]1[N:32]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:30]=[C:29]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:28]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[C:39]1([C:29]2[N:30]=[C:31]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:32]=[C:27]([C:5]3[CH:4]=[C:3]4[C:8]5=[C:7]([C:23]6[CH:22]=[CH:21][CH:20]=[CH:19][C:24]=6[N:9]5[C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=5[C:2]4([CH3:25])[CH3:1])[CH:6]=3)[N:28]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 196982-Chloro-4,6-diphenyl-1,3,5-triazineHCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 673261988,8-Dimethyl-8H-indolo[3,2,1-de]acridine-6-boronic acid

Produkt 1

HCID 680145136-(4,6-Diphenyl-1,3,5-triazin-2-yl)-8,8-dimethyl-8H-indolo[3,2,1-de]acridine

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

36 g (110.0 mmol) of 8,8-dimethyl-8H-indolo[3,2,1-de]acridine-6-boronic acid, 29.5 g (110.0 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 44.6 g (210.0 mmol) of tripotassium phosphate are suspended in 500 ml of toluene, 500 ml of dioxane and 500 ml of water. 913 mg (3.0 mmol) of tri-o-tolylphosphine and then 112 mg (0.5 mmol) of palladium (II) acetate are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene and from dichloromethane/isopropanol and finally sublimed in a high vacuum, the purity is 99.9%. The yield is 46 g (89 mmol), corresponding to 83% of theory.

Aufarbeitung

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. filtrationfiltered through silica gel
  6. washwashed three times with 200 ml of water
  7. customsubsequently evaporated to dryness
  8. customThe residue is recrystallised from toluene and from dichloromethane/isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-a6770a7d366e4c6b95e63f56fa609ed3
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08785636B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion