p-Toluenesulfonic acid → 1,10-Phenanthroline

HRID 707750

Reaktionsgleichung

Reaktionsgleichung von HRID 707750
[N:1]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][N:12]=3)[CH:7]=[C:6](N)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 6069701,10-Phenanthrolin-5-amine

Produkt 1

HCID 13181,10-PhenanthrolineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

3.05 mM of the 4-di(2-thienyl)-1,4-butanedione obtained from Step 1 described above, 3.03 mM of 1,10-phenanthroline-5-amine, and 5.4 mM of p-toluene sulfonic acid were dissolved in toluene, and then refluxed under a nitrogen current for 4 days. The refluxed mixture was cooled to room temperature, and then toluene was removed from the mixture. The remaining material was dissolved in 5 ml of 99.8% dichloromethane solution, and eluted by using a silica column to obtain 5-di(thiophen-2-yl)-1H-pyrrol-1-yl)-1,10-phenanthroline. The yield was 85%, and the structure was confirmed by using 1H NMR. The spectroscopic data thereof is as follows:

Aufarbeitung

  1. temperaturerefluxed under a nitrogen current for 4 days
  2. customtoluene was removed from the mixture
  3. dissolutionThe remaining material was dissolved in 5 ml of 99.8% dichloromethane solution
  4. washeluted

Quellen und Nachweise

ORD-Eintrag
ord-a610498926d4441ebcb1a453dfd1a538
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09175328B2

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