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1,3-Bis(4-nitrophenoxy)-2,2-bis[(4-nitrophenoxy)methyl]propane → 4,4'-((2,2-Bis((4-aminophenoxy)methyl)propane-1,3-diyl)bis(oxy))dianiline

HRID 8414
Notes
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Reaction equation

HRID 8414 reaction equation
[N+:1]([C:4]1[CH:45]=[CH:44][C:7]([O:8][CH2:9][C:10]([CH2:33][O:34][C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-])=O)=[CH:37][CH:36]=2)([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=2)[CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>O1CCCC1.[Pd]>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:10]([CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:45][CH:44]=2)([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[CH2:33][O:34][C:35]2[CH:36]=[CH:37][C:38]([NH2:41])=[CH:39][CH:40]=2)=[CH:18][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 121049911,3-Bis(4-nitrophenoxy)-2,2-bis[(4-nitrophenoxy)methyl]propaneHCID 178418361HCID 178418361, compound

Product 1

HCID 220154304,4'-((2,2-Bis((4-aminophenoxy)methyl)propane-1,3-diyl)bis(oxy))dianilineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028
Tetrahydrofuran
Solvent

Procedure

A mixture of 1,3-bis(4-nitrophenoxy)-2,2-bis [(4-nitrophenoxy)methyl]propane (15.43 grams, 24.87 mmol; prepared as described in Part B of this Example) and Pd/C 10% (1.58 grams, obtained from Aldrich Chemical Co.) was stirred for 70 hours in tetrahydrofuran (400 milliliters) under 180 pounds per square inch of hydrogen gas. The mixture was then filtered over CELITE, and the solvent was removed by evaporation under reduced pressure. The residue was recrystallized from nitrobenzene/benzene to afford pure 1,3-bis(4-aminophenoxy)-2,2-bis[(4-aminophenoxy)methyl]propane (11.17 grams, 22.31 mmol, 90 percent yield) as small light brown crystals: mp 210–211° C.; IR (KBr) 3434, 3351, 3050, 2932, 1625, 1511, 1467, 1232, 1041, 1172, 831, 523 cm−1; 1H NMR (400 MHz, DMSO-d6) δ 6.66 (d, 8H, 3J=8.4 Hz), 6.47 (d, 8H, 3J=8.4 Hz), 4.62 (s, 8H), 4.03 (s, 8H); 13C NMR (100 MHz, DMSO-d6) δ 150.14, 142.73, 115.76, 114.86, 67.06, 44.59; MS (FAB, 3-nitrobenzyl alcohol) m/e 500.3; Anal. Calcd for C33H24N4O4: C, 69.58; H, 6.44; N, 11.19. Found: C, 69.33; H, 6.78; N, 10.91.

Workup

  1. customprepared
  2. filtrationThe mixture was then filtered over CELITE
  3. customthe solvent was removed by evaporation under reduced pressure
  4. customThe residue was recrystallized from nitrobenzene/benzene

Sources & evidence

ORD record
ord-1a593854508344ba9e6124d621ab3ac1
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087752B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes