Reaktion #8514

Reaktionsgleichung

water

cyanuric chloride

1,5-bis(4-aminophenoxy)pentane

Octylamine

→

1,5-Bis[4-[N-[4,6-bis(N-octylamino)-1,3,5-triazin-2-yl]amino]phenoxy]pentane

Ausbeute 45.2%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred
2. 2
   Temperaturat reflux for 3 hours
3. 3
   TemperaturThe mixture was cooled to room temperature
4. 4
   Filtrationthe resulting gummy precipitate (like glue) was filtered
5. 5
   workup.DISSOLUTIONThe precipitate was dissolved in chloroform
6. 6
   Filtrationfiltered over silica gel
7. 7
   SonstigeThe volatiles were removed under reduced pressure

Vorschrift

A solution of cyanuric chloride (6.44 grams, 34.9 mmol; obtained from Aldrich Chemical Co.) in dry tetrahydrofuran (50 milliliters) was added dropwise to a solution of 1,5-bis(4-aminophenoxy)pentane (5.00 grams, 17.46 mmol; prepared as described in Part B of Example VIII) in dry tetrahydrofuran (100 milliliters) at −78° C. The mixture was stirred and allowed to warm up to room temperature for 2 hours. Octylamine (23.0 milliliters, 139 mmol; obtained from Aldrich Chemical Co.) was then added and the mixture was stirred at reflux for 3 hours. The mixture was cooled to room temperature, water was added, and the resulting gummy precipitate (like glue) was filtered. The precipitate was dissolved in chloroform and filtered over silica gel. The volatiles were removed under reduced pressure to afford 1,5-Bis[4-[N-[4,6-bis(N-octylamino)-1,3,5-triazin-2-yl]amino]phenoxy]pentane (7.51 grams, 7.88 mmol, 45 percent yield) as a white solid: IR (KBr) 3410, 3279, 2926, 2855, 1575, 1506, 1423, 1369, 1230, 1031, 810 cm−1.

Quelle