Reacción #8512

Ecuación de reacción

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

Rendimiento 69.0%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprepared
2. 2
   Temperaturawas heated
3. 3
   Temperaturaat reflux for 3 hours
4. 4
   TemperaturaThe mixture was then cooled
5. 5
   FiltraciónThe resulting white solid was filtered off
6. 6
   workup.DISSOLUTIONdissolved in tetrahydrofuran
7. 7
   FiltraciónThis solution was filtered over silica gel
8. 8
   Otrothe volatiles were removed under reduced pressure
9. 9
   OtroThe residue was triturated in methanol
10. 10
    Otrodried under vacuum

Procedimiento

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.

Fuente