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Potassium Carbonate → HCID 20781554, Verbindung

HRID 1660672
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1660672
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.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O.C(Cl)(Cl)Cl.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:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:11][C:12]=2[S:13][C:14]2[C:5]1=[CH:4][CH:3]=[C:2]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:14][CH:15]=1)[CH:15]=2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 109156503,7-dibromo-10-methylphenothiazine

Produkt 1

HCID 20781554HCID 20781554, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 962
Water
Lösungsmittel
HCID 6212ChloroformLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

2.50 g (6.7 mmol) of 3,7-dibromo-10-methylphenothiazine (C. Bodea and M. Terdic, Acad. Rep. Rom. 1962, 13, 81-87), 1.85 g (14.9 mmol) of 98% phenylboronic acid, 0.11 g (0.14 mmol) of bis(triphenylphosphine)palladium dichloride and 1.03 g (7.4 mmol) of potassium carbonate were heated to boiling (75° C.) under reflux under nitrogen for 5 hours in 55 ml of dimethoxyethane and 28 ml of water. The reaction mixture was cooled to room temperature and stirred further overnight. The precipitate was filtered off with suction, washed successively with 125 ml of ethanol and hot water and dried at 70° C. under reduced pressure. The crude product (2.30 g) was heated to boiling under reflux in cyclohexane for two hours. After the hot suspension had been filtered, the residue was dried, dissolved in 40 ml of methylene chloride and filtered through a silica-gel-filled glass fit. After the solvent had been removed, 1.05 g (43% of theory) of light yellow, analytically pure solid having a melting point of 239-241° C. were obtained, whose solution in chloroform fluoresced at λ=464 nm.

Aufarbeitung

  1. custom(75° C.)
  2. filtrationThe precipitate was filtered off with suction
  3. washwashed successively with 125 ml of ethanol and hot water
  4. customdried at 70° C. under reduced pressure
  5. temperatureThe crude product (2.30 g) was heated
  6. temperatureunder reflux in cyclohexane for two hours
  7. filtrationAfter the hot suspension had been filtered
  8. customthe residue was dried
  9. dissolutiondissolved in 40 ml of methylene chloride
  10. filtrationfiltered through a silica-
  11. additiongel-filled glass fit
  12. customAfter the solvent had been removed
  13. customwere obtained

Quellen und Nachweise

ORD-Eintrag
ord-feac67004ef7494a8768dbddaa96766a
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08029919B2

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