Diethanolamine → 4'-(Bis-(2-hydroxyethyl)-amino)-2,2': 6',2''-terpyridine

HRID 1373383

反応式

HRID 1373383 の反応式
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].Cl[C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:12]=[C:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH:10]=1>CO.[OH-].[Na+].C(#N)C.O.O.O.O.O.[Cl-].[Mn+2].[Cl-]>[OH:4][CH2:3][CH2:2][N:1]([C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:12]=[C:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH:10]=1)[CH2:5][CH2:6][OH:7]

参加物

7

反応物 2

HCID 8113DiethanolamineHCID 6677484'-Chloro-2,2':6',2''-terpyridine

生成物 1

HCID 107355974'-(Bis-(2-hydroxyethyl)-amino)-2,2': 6',2''-terpyridine

試薬・触媒・溶媒 4

HCID 26003Manganese chloride触媒HCID 887Methanol溶媒HCID 14798Sodium Hydroxide溶媒HCID 18373917Acetonitrile--water (1/1)溶媒

実験手順

3.41 g (17.2 mmol) of manganese(II) chloride tetrahydrate and 98 g (0.93 mol) of diethanolamine are added in succession to a mixture of 2.14 g (8 mmol) of 4′-chloro-[2,2′;6′,2″]-terpyridine in 200 ml of methanol. The mixture is heated at reflux for 14 hours, cooled and concentrated. The residue so obtained is stirred in 250 ml of sodium hydroxide solution in acetonitrile/water 1:1 (v/v, pH>12) for 20 hours in air. Acetonitrile is removed using a rotary evaporator and the aqueous portion is extracted three times with chloroform. The organic extract is filtered over sodium sulfate and concentrated. Diethyl ether is added to the residue and the mixture is stirred and filtered, yielding 2-[(2-hydroxy-ethyl)-[2,2′;6′,2″]-terpyridin-4′-yl-amino]-ethanol in the form of a white solid. 1H-NMR (360 MHz, CD3OD): 3.76 (t, J=5.4 Hz, 4 H); 3.85 (t, J=5.4 Hz, 4H); 7.38–7.47 (tm, 2H); 7.69 (s, 2H); 7.94 (dt, J=8.1, 1.8 Hz, 2H); 8.53 (d, J=8.1 Hz, 2H); 8.58–8.65 (dm, 2H).

後処理

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 14 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe residue so obtained
  6. customAcetonitrile is removed
  7. customa rotary evaporator
  8. extractionthe aqueous portion is extracted three times with chloroform
  9. extractionThe organic extract
  10. filtrationis filtered over sodium sulfate
  11. concentrationconcentrated
  12. additionDiethyl ether is added to the residue
  13. filtrationfiltered

出典と根拠

ORDレコード
ord-43d5857c891e4df7ba62dc0b60aee08f
出典データセット
uspto-grants-2007_01
特許番号
US07161005B2

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