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

HRID 982597

Reaction equation

HRID 982597 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[NH2:10][C:11]1[CH:46]=[CH:45][C:14]([O:15][CH2:16][C:17]([CH2:36][O:37][C:38]2[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=2)([CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)[CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)=[CH:13][CH:12]=1.[CH2:47]([NH2:55])[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54].O>O1CCCC1>[CH2:47]([NH:55][C:2]1[N:4]=[C:5]([NH:55][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[N:7]=[C:8]([NH:44][C:41]2[CH:40]=[CH:39][C:38]([O:37][CH2:36][C:17]([CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]([NH:26][C:2]4[N:4]=[C:5]([NH:55][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[N:7]=[C:8]([NH:55][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[N:1]=4)=[CH:24][CH:25]=3)([CH2:27][O:28][C:29]3[CH:34]=[CH:33][C:32]([NH:35][C:2]4[N:4]=[C:5]([NH:55][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[N:7]=[C:8]([NH:55][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[N:1]=4)=[CH:31][CH:30]=3)[CH2:16][O:15][C:14]3[CH:13]=[CH:12][C:11]([NH:10][C:2]4[N:4]=[C:5]([NH:55][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[N:7]=[C:8]([NH:55][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[N:1]=4)=[CH:46][CH:45]=3)=[CH:43][CH:42]=2)[N:1]=1)[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]

Participants

6

Reactant 4

HCID 962WaterHCID 7954Cyanuric chlorideHCID 8143OctylamineHCID 220154304,4'-((2,2-Bis((4-aminophenoxy)methyl)propane-1,3-diyl)bis(oxy))dianiline

Product 1

HCID 220154331,3-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]propaneYield 70.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  1. stirringthe mixture was stirred
  2. temperatureat reflux for 3 hours
  3. temperatureThe mixture was subsequently cooled to room temperature
  4. filtrationa gummy precipitate (like glue) was filtered
  5. dissolutionThe precipitate was dissolved in hot dimethylformamide
  6. additionethanol was added (3 liters), and trituration
  7. filtrationThe solid was then filtered
  8. washwashed with methanol
  9. customdried for 2 days under reduced pressure

Sources & evidence

ORD record
ord-1510ebdefa9344349d6437e344470215
Source dataset
uspto-grants-2005_03
Patent number
US06860928B2

Linked notes

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