2-Chloro-4,6-diphenyl-1,3,5-triazine → 7-Bromo-10-(4,6-diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

HRID 2275925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2275925
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]=[C:8]3[C:15]([CH3:23])([CH3:22])[C:16]4[C:21]([C:7]3=[CH:6][C:5]2=1)=[CH:20][CH:19]=[CH:18][CH:17]=4.[H-].[Na+].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>CN(C)C=O.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:27]1[N:32]=[C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:30]=[C:29]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[N:28]=1)[C:10]1[CH:9]=[C:8]3[C:15]([CH3:23])([CH3:22])[C:16]4[C:21]([C:7]3=[CH:6][C:5]2=1)=[CH:20][CH:19]=[CH:18][CH:17]=4

Komponenten

6

Edukt 3

HCID 196982-Chloro-4,6-diphenyl-1,3,5-triazineHCID 24758Sodium hydrideHCID 667977897-Bromo-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Produkt 1

HCID 667979517-Bromo-10-(4,6-diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

25.5 g (70.4 mmol) of 7-bromo-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene are dissolved in 400 ml of dimethylformamide under a protective-gas atmosphere, and 3.1 g of 60% NaH in mineral oil (78 mol) are added. After 1 h at room temperature, a solution of 2-chloro-4,6-diphenyl-1,3,5-triazine (22.6 g, 84.5 mmol) in 100 ml of THF is added dropwise. The reaction mixture is stirred at room temperature for 12 h. After this time, the reaction mixture is poured onto ice and extracted three times with dichloromethane. The combined organic phases are dried over Na2SO4 and evaporated. The residue is recrystallised from toluene. Yield: 40 g (67 mmol), 95% of theory.

Aufarbeitung

  1. additionare added
  2. additionAfter this time, the reaction mixture is poured onto ice
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated
  6. customThe residue is recrystallised from toluene

Quellen und Nachweise

ORD-Eintrag
ord-335c300690054a5c991c04d55e1a3423
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126970B2

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