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

HRID 640669

반응식

HRID 640669 반응식
[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]

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 26003Manganese chloride촉매HCID 887Methanol용매HCID 14798Sodium Hydroxide용매HCID 18373917Acetonitrile--water (1/1)용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2dafbd4d340e413f91e46ebf9f313caa
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07692004B2

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