Reaktion #69051

Reaktionsgleichung

ethyl acetate

DIPEA

2-methylaminomethyl-1,3 dioxolane

CC-12

1-(4-methylbenzamido)-2-(chloroacetamido)-anthraquinone

→

1-(4-methylbenzamido)-2-[2-[(1,3-dioxolan-2-ylmethyl)(methyl)amino]acetylamino]-anthraquinone

Ausbeute 43.0%

Lösungsmittel

EtOH

n-hexane

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThis mixture was heated
2. 2
   Temperaturunder reflux for 16 hours
3. 3
   SonstigeAfter the completion of the reaction
4. 4
   Filtrationthe mixture was filtered
5. 5
   Einengenthe filtrate was concentrated by reduced pressure concentrator (such as Vacuum Evaporator)
6. 6
   ExtraktionThe residue was extracted with ethyl acetate for several times
7. 7
   SonstigeThe extract was dried on magnesium sulfate
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   WaschenThe crude product was washed with ethyl acetate/hexane
10. 10
    SonstigeFinally, the crude product was recrystallized in hot ethanol
11. 11
    Sonstigeto obtain a kelly green compound CC-36

Vorschrift

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 2-methylaminomethyl-1,3 dioxolane (0.91 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 kelly green compound CC-36. Mol. Wt.: 513.5412 (C29H27N3O6); Rf: 0.31 (ethyl acetate: n-hexane=1:2); Yield: 43%; Mp.: 156-157° C. (EtOH); HRMS (EI) m/z: calcd [M]+, 513.1900 (C29H27N3O6+). Found, 513.1902. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 2.18 (s, 3H, —CH3), 2.44 (s, 3H, —CH3), 2.54 (d, J=8.7 Hz, 2H, —NCH2—), 3.26 (s, 2H, —CH2N—), 3.52-3.55 (m, 2H, —OCH2—), 3.72-3.77 (m, 2H, —OCH2—), 4.58 (t, J=4.5 Hz, 1H, —OCHO—), 7.43 (d, J=7.8 Hz, 2H, Ar—H), 7.88-7.92 (m, 2H, Ar—H), 8.04 (d, J=8.1 Hz, 2H, Ar—H), 8.10-8.19 (m, 2H, Ar—H), 8.27 (d, J=8.4 Hz, 1H, Ar—H), 8.70 (d, J=8.7 Hz, 1H, Ar—H), 10.15 (s, 1H, Ar—NH—), 10.53 (s, 1H, Ar—NH—); 13C-NMR (75 MHz, DMSO-d6) δ (ppm): 20.87, 43.49, 59.43, 61.73, 63.91, 102.61, 125.50, 126.31, 126.48, 126.90, 127.89, 128.06, 129.06, 129.31, 130.75, 132.33, 134.16, 134.38, 134.45, 140.42, 142.29, 166.25 (NCO), 169.59 (NCO), 181.46 (CO), 183.70 (CO).

Quelle