1,5-Dichloroanthraquinone → 1,5-Bis((2-(dimethylamino)ethyl)(methyl)amino)anthracene-9,10-dione

HRID 522936

Reaktionsgleichung

Reaktionsgleichung von HRID 522936
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](Cl)[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][NH:23][CH3:24]>O>[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][N:23]([CH3:24])[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([N:23]([CH2:22][CH2:21][N:20]([CH3:25])[CH3:19])[CH3:24])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 67111,5-DichloroanthraquinoneHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-

Produkt 1

HCID 592291181,5-Bis((2-(dimethylamino)ethyl)(methyl)amino)anthracene-9,10-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1,5-dichloroanthraquinone (5.5 g, 20 mmol) and N,N,N′-trimethylethylenediamine (40 ml) was refluxed for 18 h. The mixture was cooled to room temperature, diluted with water (400 mL) and extracted with chloroform (2×200 mL). The combined organic layer was washed with water, brine, dried over MgSO4 and evaporated to dryness. The residue thus obtained was purified by silica gel flash chromatography [CHCl3/MeOH/Et3N (44:5:1)] to provide Compound 9. Abs (max, PBS pH 7.4)=508 nm. The structure of Compound 9 is given below:

Aufarbeitung

  1. temperaturewas refluxed for 18 h
  2. extractionextracted with chloroform (2×200 mL)
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe residue thus obtained
  7. customwas purified by silica gel flash chromatography [CHCl3/MeOH/Et3N (44:5:1)]

Quellen und Nachweise

ORD-Eintrag
ord-e3151e542a2f4975a8558c2400efa07e
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334281B2

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