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

反応式

HRID 8414 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1a593854508344ba9e6124d621ab3ac1
出典データセット
uspto-grants-2006_08
特許番号
US07087752B2

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