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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 982597Erstellt: 24. Oktober 2026

Water → 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

https://huagongshe.com/de/reaction/982597

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktWaterHCID 962—
EduktCyanuric chlorideHCID 7954—
EduktOctylamineHCID 8143—
Edukt4,4'-((2,2-Bis((4-aminophenoxy)methyl)propane-1,3-diyl)bis(oxy))dianilineHCID 22015430—
LösungsmittelTetrahydrofuranHCID 8028—
Produkt1,3-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]propaneHCID 2201543370,8%

Reaktionsschritte

A solution of cyanuric chloride (36.9 grams, 200 mmol; obtained from Aldrich Chemical Co., Milwaukee, Wis.) in 100 milliliters of dry tetrahydrofuran was added dropwise to a solution of 1,3-bis(4-aminophenoxy)-2,2-bis[(4-aminophenoxy)methyl]propane (25 grams, 50.0 mmol, prepared as described in Part C of Example I) in 500 milliliters of dry tetrahydrofuran at −78° C. The mixture was stirred and allowed to warm up to room temperature for 2 hours. Octylamine (165 milliliters, 1.00 mol; obtained from Aldrich Chemical Co.) was then added and the mixture was stirred at reflux for 3 hours. The mixture was subsequently cooled to room temperature, water was added, and a gummy precipitate (like glue) was filtered. The precipitate was dissolved in hot dimethylformamide, ethanol was added (3 liters), and trituration was done until the product became a fine solid. The solid was then filtered, washed with methanol, and dried for 2 days under reduced pressure to afford tetrakis[(4-[N-[4,6-bis(N-octylamino)-1,3,5-triazin-2-yl]amino]phenoxy)methyl]methane (65.0 grams, 35.4 mmol, 70 percent yield) as a white solid: 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) δ8.11 (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) δ165.54, 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.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS06860928B2
Quelldatensatzuspto-grants-2005_03
ORD IDord-1510ebdefa9344349d6437e344470215
Quellennotizuspto-grants-2005_03