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

HRID 640669

Reaktionsgleichung

Reaktionsgleichung von HRID 640669
[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]

Komponenten

7

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 26003Manganese chlorideKatalysatorHCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittelHCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2dafbd4d340e413f91e46ebf9f313caa
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07692004B2

Verknüpfte Notizen

Wird geladen…