Cyanuric chloride → 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

HRID 982595

反応式

HRID 982595 の反応式
[NH2:1][C:2]1[CH:37]=[CH:36][C:5]([O:6][CH2:7][C:8]([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)[CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.O1CCCC1.[N:43]1[C:50](Cl)=[N:49][C:47]([Cl:48])=[N:46][C:44]=1[Cl:45].C([O-])([O-])=O.[Na+].[Na+]>CC(C)=O.O>[Cl:48][C:47]1[N:46]=[C:44]([Cl:45])[N:43]=[C:50]([NH:35][C:32]2[CH:31]=[CH:30][C:29]([O:28][CH2:27][C:8]([CH2:9][O:10][C:11]3[CH:12]=[CH:13][C:14]([NH:17][C:50]4[N:49]=[C:47]([Cl:48])[N:46]=[C:44]([Cl:45])[N:43]=4)=[CH:15][CH:16]=3)([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:50]4[N:49]=[C:47]([Cl:48])[N:46]=[C:44]([Cl:45])[N:43]=4)=[CH:22][CH:21]=3)[CH2:7][O:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:50]4[N:49]=[C:47]([Cl:48])[N:46]=[C:44]([Cl:45])[N:43]=4)=[CH:37][CH:36]=3)=[CH:34][CH:33]=2)[N:49]=1

参加物

7

反応物 4

HCID 7954Cyanuric chlorideHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 220154304,4'-((2,2-Bis((4-aminophenoxy)methyl)propane-1,3-diyl)bis(oxy))dianiline

生成物 1

HCID 220154391,3-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収率 84%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒2 回HCID 962Water溶媒

反応条件

温度
-10 °C

実験手順

A solution of 1,3-bis(4-aminophenoxy)-2,2-bis[(4-aminophenoxy)methyl]propane (5.00 grams, 10.0 mmol; prepared as described in Part C of this Example) in 120 milliliters of a mixture of dry acetone and tetrahydrofuran (1:1 (v/v)) was added dropwise to a solution of cyanuric chloride (7.75 grams, 42.0 mmol: obtained from Aldrich Chemical Co.) in 200 milliliters of dry acetone at −10° C. This mixture was stirred for 1 hour at −10° C. and was then added, with Na2CO3 (4.45 grams, 42.0 mmol), to 1.5 liters of cold water to give a precipitate. The white solid was filtered off, dried, and dissolved in dichloromethane to remove insoluble material (hydrolyzed product). The resulting solution was filtered over CELITE and dried with magnesium sulfate. Volatiles were removed under reduced pressure, and the residue was dried under vacuum to afford pure 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 (9.20 grams, 8.42 mmol, 84 percent yield) as a white solid: softening point 143-145° C.; mp 240-250° C.: IR (KBr) 3366, 3268, 3123, 2947, 1609, 1550, 1506, 1386, 1318, 1219, 1167, 1019, 846, 829, 794 cm−1; 1H NMR (400 MHz, CDCl3) δ7.47 (s, 4H), 7.40 (d, 8H, 3J=9.0 Hz), 6.96 (d, 8H, 3J=9.0 Hz), 4.36 (s, 8H); 13C NMR (100 MHz, CDCl3) δ171.46, 164.44, 156.93, 129.12, 123.93, 115.39, 66.90, 45.11; MS (FAB, 3-nitrobenzyl alcohol) m/e 1092.7; Anal. Calcd for C41H28Cl8N16O4: C, 45.08; H, 2.58; N, 20.52. Found: C, 45.07; H, 2.58; N, 20.12.

後処理

  1. customprepared
  2. customto give a precipitate
  3. filtrationThe white solid was filtered off
  4. customdried
  5. dissolutiondissolved in dichloromethane
  6. customto remove insoluble material (hydrolyzed product)
  7. filtrationThe resulting solution was filtered over CELITE
  8. dry with materialdried with magnesium sulfate
  9. customVolatiles were removed under reduced pressure
  10. customthe residue was dried under vacuum

出典と根拠

ORDレコード
ord-172dd81ab7534460867243a637765522
出典データセット
uspto-grants-2005_03
特許番号
US06860928B2

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