Reaktion #8512

Reaktionsgleichung

1,3-bis(4-[N-(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenoxy)-2,2-bis[(4-[N-(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenoxy)methyl]propane

octylamine

NaOH

methanol

→

1,3-bis(4-[N-(2,4-bis(N-octylamino)-1,3,5-triazin-6-yl)amino]phenoxy)-2,2-bis [(4-[N-(2,4-bis(N-octylamino)—1,3,5-triazin-6-yl)amino]phenoxy)methyl]propane

Ausbeute 69.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   Temperaturwas heated
3. 3
   Temperaturat reflux for 3 hours
4. 4
   TemperaturThe mixture was then cooled
5. 5
   FiltrationThe resulting white solid was filtered off
6. 6
   workup.DISSOLUTIONdissolved in tetrahydrofuran
7. 7
   FiltrationThis solution was filtered over silica gel
8. 8
   Sonstigethe volatiles were removed under reduced pressure
9. 9
   SonstigeThe residue was triturated in methanol
10. 10
    Sonstigedried under vacuum

Vorschrift

A mixture of 1,3-bis(4-[N-(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenoxy)-2,2-bis[(4-[N-(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenoxy)methyl]propane (3.88 grams, 3.55 mmol; prepared as described in Part D of this Example) and octylamine (11.7 milliliters, 71.0 mmol; obtained from Aldrich Chemical Co.) in dioxane (30 milliliters) was heated at reflux for 3 hours. The mixture was then cooled and added to 400 milliliters of a solution of 1 Normal NaOH and methanol (1:1 (v/v)). The resulting white solid was filtered off and dissolved in tetrahydrofuran. This solution was filtered over silica gel, and the volatiles were removed under reduced pressure. The residue was triturated in methanol and then dried under vacuum to afford pure 1,3-bis(4-[N-(2,4-bis(N-octylamino)-1,3,5-triazin-6-yl)amino]phenoxy)-2,2-bis [(4-[N-(2,4-bis(N-octylamino)—1,3,5-triazin-6-yl)amino]phenoxy)methyl]propane (4.50 grams, 2.45 mmol, 69 percent yield) as white powder: softening point 94–96° C.;. IR (KBr) 3434, 3274, 2925, 2854, 1579, 1506, 1421, 1367, 1226, 1030, 810 cm−1; 1H NMR (400 MHz, DMSO-d6, 373° K.) δ 8.11 (s, 4H), 7.60 (d, 8H, 3J=8.9 Hz), 6.84 (d, 8H, 3J=8.9 Hz), 6.12 (s, 8H), 4.25 (s, 8H), 3.26 (td, 16H, 3Jt=6.6 Hz, 3Jd=6.6 Hz), 1.53 (m, 16H), 1.29 (m, 80H), 0.86 (t, 24H, 3J=7.1 Hz); 13C NMR (100 MHz, DMSO-d6, 373° K.) δ 165.54, 163.77, 153.31, 133.96, 120.76, 114.27, 67.15, 44.47, 39.61, 30.56, 28.87, 28.14, 27.96, 25.90, 21.29, 13.00; MS (FAB, 3-nitrobenzyl alcohol) m/e 1834.6; Anal. Calcd for C105H172N24O4: C, 68.74; H, 9.45; N, 18.32. Found: C, 68.31; H, 9.58; N, 18.34.

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