반응 #8514

반응 방정식

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

수율 45.2%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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.

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