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

HRID 982599

Reaktionsgleichung

Reaktionsgleichung von HRID 982599
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[NH2:10][C:11]1[CH:30]=[CH:29][C:14]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=2)=[CH:13][CH:12]=1.[CH2:31]([NH2:39])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].O>O1CCCC1>[CH2:31]([NH:39][C:2]1[N:4]=[C:5]([NH:39][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[N:7]=[C:8]([NH:28][C:25]2[CH:24]=[CH:23][C:22]([O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][O:15][C:14]3[CH:13]=[CH:12][C:11]([NH:10][C:2]4[N:4]=[C:5]([NH:39][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[N:7]=[C:8]([NH:39][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[N:1]=4)=[CH:30][CH:29]=3)=[CH:27][CH:26]=2)[N:1]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7954Cyanuric chlorideHCID 8143OctylamineHCID 141731,5-Bis(p-aminophenoxy)pentane

Produkt 1

HCID 220154291,5-Bis[4-[n-[4,6-bis(n-octylamino)-1,3,5-triazin-2-yl]amino]phenoxy]pentaneAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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 worm 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.

Aufarbeitung

  1. stirringthe mixture was stirred
  2. temperatureat reflux for 3 hours
  3. filtrationthe resulting gummy precipitate (like glue) was filtered
  4. dissolutionThe precipitate was dissolved in chloroform
  5. filtrationfiltered over silica gel
  6. customThe volatiles were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-67ea16f90f674b8f9cac90968548fe34
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06860928B2

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