Cyanuric chloride → 2,4-Bis(4-ethynylphenyl)-6-phenyl-1,3,5-triazine

HRID 615250

Reaktionsgleichung

Reaktionsgleichung von HRID 615250
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[C:10]1([Mg]Br)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C[Si](C)(C)[C:20]#[C:21][C:22]1[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=1.[Mg]>O1CCCC1>[C:10]1([C:2]2[N:4]=[C:5]([C:25]3[CH:26]=[CH:27][C:22]([C:21]#[CH:20])=[CH:23][CH:24]=3)[N:7]=[C:8]([C:25]3[CH:26]=[CH:27][C:22]([C:21]#[CH:20])=[CH:23][CH:24]=3)[N:1]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 7954Cyanuric chlorideHCID 4226980(4-Bromophenylethynyl)trimethylsilaneHCID 5462224MagnesiumHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 204296802,4-Bis(4-ethynylphenyl)-6-phenyl-1,3,5-triazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

One mole of cyanuric chloride was treated with one mole of phenylmagnesium bromide as described in Step I of Example I. The product of this reaction (2.3 g, 0.01 mole) in 25 ml of tetrahydrofuran (THF) was added slowly to a refluxing solution of the Grignard reagent prepared from 1-(trimethylsilyl)-2-(4-bromophenyl)acetylene (0.03 moles) and magnesium (0.75 g). The solution was stirred overnight, filtered, and the solvent removed. To the residue which remained was added a solution of KOH (10.0 g) in water (5 ml), anhydrous ethanol (100 ml) and dioxane (100 ml). The resulting mixture was heated for 2.5 hours at 60° C., filtered, and the solvent removed. Chromatographic separation of the resulting residue yielded a yellow solid, 6-phenyl-2,4-bis(4-ethynylphenyl)-s-triazine, which melted at approximately 215° C. with rapid polymerization.

Aufarbeitung

  1. filtrationfiltered
  2. customthe solvent removed
  3. additionTo the residue which remained was added a solution of KOH (10.0 g) in water (5 ml), anhydrous ethanol (100 ml) and dioxane (100 ml)
  4. filtrationfiltered
  5. customthe solvent removed
  6. customChromatographic separation of the resulting residue

Quellen und Nachweise

ORD-Eintrag
ord-4bdb074b18c7410395a8aad3486e9c9b
Quelldatensatz
uspto-grants-1985_02
Patentnummer
US04497951

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