Cyanuric chloride → Bis-(m-ethynylphenoxy)-chloro-1,3,5-triazine

HRID 27579

Reaktionsgleichung

Reaktionsgleichung von HRID 27579
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[CH:2].[OH-:10].[Na+].[N:12]1[C:19](Cl)=[N:18][C:16]([Cl:17])=[N:15][C:13]=1Cl>CC(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][C:13]1[N:15]=[C:16]([Cl:17])[N:18]=[C:19]([O:10][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([C:1]#[CH:2])[CH:8]=2)[N:12]=1)#[CH:2]

Komponenten

5

Edukt 3

HCID 7954Cyanuric chlorideHCID 14798Sodium HydroxideHCID 139144m-Ethynylphenol

Produkt 1

HCID 23343155Bis-(m-ethynylphenoxy)-chloro-1,3,5-triazineAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

The bis-(m-ethynylphenoxy)-chloro-1,3,5-triazine is prepared by first adding m-ethynylphenol (11.4 g, 0.097 mole) in 20 ml of a 5 N NaOH dropwise to a stirred solution of cyanuric chloride (9.22 g, 0.05 mole) in 50 ml of acetone with stirring at 15°-18° C. After stirring for one hour at this temperature, the resulting mixture is filtered to remove a white solid which is washed with water and dried in vacuum overnight at 35° C. The yield of the product is 16.14 g (yield of 95.8%). The product has a melting point of 121°-125° C. which increases to 127°-128° C. upon one recrystallization from chloroform/heptane. This product is analyzed by NMR and determined to be bis-(m-ethynylphenoxy)-chloro-1,3,5-triazine represented by the formula:

Aufarbeitung

  1. stirringAfter stirring for one hour at this temperature
  2. filtrationthe resulting mixture is filtered
  3. customto remove a white solid which
  4. washis washed with water
  5. customdried in vacuum overnight at 35° C
  6. temperatureincreases to 127°-128° C. upon one recrystallization from chloroform/heptane

Quellen und Nachweise

ORD-Eintrag
ord-81fabdb1a40044d5a7054b95e48411d2
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04221895

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