Methanol → 3,7-Bis(2',2'-diphenylvinyl)-10-p-tolylphenothiazine

HRID 2287297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2287297
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:8]3[C:13]([S:14][C:15]=2[CH:16]=1)=[CH:12][C:11]([CH:17]=O)=[CH:10][CH:9]=3)=O.[C:26]1([CH:32](P(=O)(OCC)OCC)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH3:47][C:48]([CH3:51])([O-])[CH3:49].[K+].CO>CN(C=O)C>[C:33]1([C:32]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:1][C:3]2[CH:4]=[CH:5][C:6]3[N:7]([C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=4)[C:8]4[C:13]([S:14][C:15]=3[CH:16]=2)=[CH:12][C:11]([CH:17]=[C:47]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:15][CH:16]=2)[C:48]2[CH:51]=[CH:13][CH:8]=[CH:9][CH:49]=2)=[CH:10][CH:9]=4)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 10267017Diethyl benzhydrylphosphonateHCID 187044763,7-Diformyl-10-p-tolylphenothiazineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 187044733,7-Bis(2',2'-diphenylvinyl)-10-p-tolylphenothiazineAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In 20 ml of DMF were dissolved 2.0 g (5.8 mmol) of 3,7-diformyl-10-p-tolylphenothiazine (2b) and 4.0 g (13.2 mmol) of diethyl diphenylmethylphosphonate (3a). Thereto was gradually added 1.5 g (13.4 mmol) of potassium t-butoxide. After the mixture was reacted overnight, 10 ml of methanol was added thereto. The crystals precipitated were taken out by filtration, dissolved in chloroform, purified by silica gel column chromatography (toluene), and then recrystallized from a chloroform/hexane mixed solvent to obtain 1.48 g of the target compound.

Aufarbeitung

  1. customAfter the mixture was reacted overnight
  2. customThe crystals precipitated
  3. filtrationwere taken out by filtration
  4. dissolutiondissolved in chloroform
  5. custompurified by silica gel column chromatography (toluene)
  6. customrecrystallized from a chloroform/hexane mixed solvent

Quellen und Nachweise

ORD-Eintrag
ord-8ef1f08c26b04b1f875d9eac75c9cfcf
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06083651

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