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Dimethylamine → 1-(4-Methylbenzamido)-2-[2-(dimethylamino)acetylamino]anthraquinone

HRID 40772
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 40772
[CH3:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([NH:8][C:9]2[C:22]3[C:21](=[O:23])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14](=[O:24])[C:13]=3[CH:12]=[CH:11][C:10]=2[NH:25][C:26](=[O:29])[CH2:27]Cl)=[O:7])=[CH:4][CH:3]=1.C[CH2:33][N:34](C(C)C)[CH:35](C)C.CNC.C(OCC)(=O)C>O1CCCC1.CCO.CCCCCC>[CH3:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([NH:8][C:9]2[C:22]3[C:21](=[O:23])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14](=[O:24])[C:13]=3[CH:12]=[CH:11][C:10]=2[NH:25][C:26](=[O:29])[CH2:27][N:34]([CH3:35])[CH3:33])=[O:7])=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 674DimethylamineHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 533741991-(4-Methylbenzamido)-2-(chloroacetamido)-anthraquinone

Produkt 1

HCID 533745851-(4-Methylbenzamido)-2-[2-(dimethylamino)acetylamino]anthraquinoneAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Compound CC-12 (0.86 g, 2 mmole) was dissolved in anhydrous tetrahydrofuran (30 ml), and to the solution was added successively with DIPEA (1 ml, 6 mmole) and dimethylamine (0.8 ml, 8 mmole) under stirring for 5 to 10 minutes. This mixture was heated under reflux for 16 hours. After the completion of the reaction, the mixture was filtered, and the filtrate was concentrated by reduced pressure concentrator (such as Vacuum Evaporator). The residue was extracted with ethyl acetate for several times. The extract was dried on magnesium sulfate, and concentrated under reduced pressure. The crude product was washed with ethyl acetate/hexane. Finally, the crude product was recrystallized in hot ethanol to obtain a yellowish-brown compound CC-35. Mol. Wt.: 441.4785 (C26H23N3O4); Rf: 0.33 (ethyl acetate:n-hexane=1:2); Yield: 54%; Mp.: 190-191° C. (EtOH); HRMS (EI) m/z: calcd [M]+, 441.1689 (C26H23N3O4+). Found, 441.1689. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 2.11 (s, 6H, —NCH3), 2.44 (s, 3H, —CH3), 3.09 (s, 2H, —CH2N—), 7.43 (d, J=8.1 Hz, 1H, Ar—H), 7.88-7.91 (m, 2H, Ar—H), 8.11-8.19 (m, 2H, Ar—H), 8.26 (d, J=8.7 Hz, 1H, Ar—H), 8.64 (d, J=8.4 Hz, 1H, Ar—H), 10.16 (s, 1H, Ar—NH—), 10.54 (s, 1H, Ar—NH—); 13C-NMR (75 MHz, DMSO-d6) δ (ppm): 20.86, 45.16, 62.82, 125.73, 126.30, 126.47, 127.79, 127.99, 128.12, 128.89, 129.09, 129.39, 130.93, 132.32, 134.13, 134.36, 134.43, 140.34, 142.23, 166.35 (NCO), 169.14 (NCO), 181.45 (CO), 183.63 (CO).

Aufarbeitung

  1. temperatureThis mixture was heated
  2. temperatureunder reflux for 16 hours
  3. customAfter the completion of the reaction
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate was concentrated by reduced pressure concentrator (such as Vacuum Evaporator)
  6. extractionThe residue was extracted with ethyl acetate for several times
  7. customThe extract was dried on magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washThe crude product was washed with ethyl acetate/hexane
  10. customFinally, the crude product was recrystallized in hot ethanol
  11. customto obtain a yellowish-brown compound CC-35

Quellen und Nachweise

ORD-Eintrag
ord-9e8eb06bfc6c488bacc0a7acd16354d5
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08530465B2

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