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Potassium Carbonate → HCID 59609618, Verbindung

HRID 1660675
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1660675
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:17])[C:7]3[C:12]([S:13][C:14]=2[CH:15]=1)=[CH:11][C:10](Br)=[CH:9][CH:8]=3.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:17][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([C:19]3[CH:20]=[CH:21][C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:18]=3)=[CH:11][C:12]=2[S:13][C:14]2[C:5]1=[CH:4][CH:3]=[C:2]([C:20]1[CH:19]=[CH:18][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=1)[CH:15]=2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 2734375(Naphthalen-2-yl)boronic acidHCID 109156503,7-dibromo-10-methylphenothiazine

Produkt 1

HCID 59609618HCID 59609618, VerbindungAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 962WaterLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

9.30 g (25.1 mmol) of 3,7-dibromo-10-methylphenothiazine, 9.50 g (55.2 mmol) of 2-naphthylboronic acid, 0.407 g (0.50 mmol) of bis(triphenylphosphine)palladium dichloride and 3.80 g (27.5 mmol) of potassium carbonate were heated to boiling under reflux under nitrogen for 5 hours in 204 ml of dimethoxyethane and 101 ml of water. The reaction mixture was cooled to room temperature, stirred further overnight and then filtered. The residue was washed with 470 ml of ethanol and hot water, and then dried at 70° C. under reduced pressure. The solid was dissolved in 200 ml of methylene chloride and filtered through silica gel. After the solvent had been removed under reduced pressure, 9.6 g of greenish-yellow solid were obtained (melting point 276-281° C.) and were recrystallized from 500 ml of toluene. 7.10 g (81% of theory) of analytically pure, shiny yellow microcrystals having a melting point of 285-289° C. were obtained, whose solution in chloroform fluoresced at λ=402 nm.

Aufarbeitung

  1. filtrationfiltered
  2. washThe residue was washed with 470 ml of ethanol and hot water
  3. customdried at 70° C. under reduced pressure
  4. dissolutionThe solid was dissolved in 200 ml of methylene chloride
  5. filtrationfiltered through silica gel
  6. customAfter the solvent had been removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-21ae7a7d8b3b47eeab4afbcfebdef308
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08029919B2

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