Pyrrole → 5,10,15,20-Tetrakis(1-methylimidazol-5-yl)porphyrin

HRID 458085

Reaktionsgleichung

Reaktionsgleichung von HRID 458085
[CH3:1][N:2]1[C:6]([CH:7]=O)=[CH:5][N:4]=[CH:3]1.[NH:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1>C(O)(=O)CC>[CH3:1][N:2]1[C:6]([C:7]2[C:13]3[NH:9][C:10]([C:7]([C:6]4[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=4)=[C:10]4[N:9]=[C:13]([C:7]([C:6]5[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=5)=[C:10]5[NH:9][C:13](=[C:7]([C:6]6[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=6)[C:10]6[CH:11]=[CH:12][C:13]=2[N:9]=6)[CH:12]=[CH:11]5)[CH:12]=[CH:11]4)=[CH:11][CH:12]=3)=[CH:5][N:4]=[CH:3]1

Komponenten

4

Edukt 2

HCID 8027PyrroleHCID 5735921-methyl-1H-imidazole-5-carbaldehyde

Produkt 1

HCID 1360826025,10,15,20-Tetrakis(1-methylimidazol-5-yl)porphyrinAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1032Propionic AcidLösungsmittel

Versuchsvorschrift

To a refluxing solution of propionic acid (400 mL) and 1-methylimidazole-5-carboxaldehyde (53, 2.0 g, 18.16 mmol), prepared according to literature procedure (Dener, J. M.; Zhang, L-H.; Rapoport, H. J. Org. Chem. 1993, 58, 1159–1166), was added pyrrole (1.26 mL, 18.16 mmol). The reaction was covered with foil then heated under reflux for 5 h. Upon cooling, the reaction mixture was exposed to air for 60 h. The propionic acid was then removed by vacuum distillation. The residue was dissolved in 10% MeOH/CH2Cl2, then adsorbed onto silica gel (6 g). Purification by column chromatography (gradient elution, 5–10% MeOH/CH2Cl2) provided porphyrin 54 as a purple solid (600 mg, 21%): 1H NMR (300 MHz. CDCl3) δ −2.80,–2.75 s, 2H. atropisomer NH). 3.42–3.58 (multiple s, 12H. atropisomer N—CH3). 7.87–7.98 (multiple s. 4H. atropisomer), 8.06 (s, 4H), 8.95–8.99 (multiple s, 8H. atropisomer).

Aufarbeitung

  1. temperaturethen heated
  2. temperatureunder reflux for 5 h
  3. temperatureUpon cooling
  4. customThe propionic acid was then removed by vacuum distillation
  5. dissolutionThe residue was dissolved in 10% MeOH/CH2Cl2
  6. customPurification
  7. washby column chromatography (gradient elution, 5–10% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-136b70822aa942afaf50eca4ded24ee3
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189707B2

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