Reacción #69048

Ecuación de reacción

ethyl acetate

pyridine

4-toluoyl chloride

1,2-diaminoanthraquinone

tetrahydrofuran

→

1,2-bis-(4-methylbenzamido)-anthraquinone

Rendimiento 62.0%

Disolventes

EtOH

n-hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThen, the mixture was stirred within a mini-reactor in an oil bath at temperature of 120-130° C. for 3 hours
2. 2
   OtroAfter the completion of the reaction
3. 3
   Filtraciónthe mixture was filtered
4. 4
   Concentraciónthe filtrate was concentrated by reduced pressure concentrator (such as Vacuum Evaporator)
5. 5
   ExtracciónThe residue was extracted with ethyl acetate for several times
6. 6
   OtroThe extract was dried on magnesium sulfate
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   LavadoThe crude product was washed with ethyl acetate/hexane
9. 9
   OtroFinally, the crude product was recrystallized in hot ethanol
10. 10
    Otroto obtain a drab compound CC-04

Procedimiento

1,2-diaminoanthraquinone (0.92 g, 4 mmole) was dissolved in anhydrous tetrahydrofuran (30 ml). To the solution, pyridine (0.5 ml), and 4-toluoyl chloride (1.6 ml, 12 mmole) were added successively at room temperature and the mixture was stirred for 5 to 10 minutes. Then, the mixture was stirred within a mini-reactor in an oil bath at temperature of 120-130° C. for 3 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 drab compound CC-04. Mol. Wt.: 474.5067 (C30H22N2O4); Rf: 0.51 (ethyl acetate:n-hexane=1:2); Yield: 62%; Mp.: 227-229° C. (EtOH); HRMS (EI) m/z: calcd [M]+, 474.1580 (C30H22N2O4+). Found, 474.1572. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 2.36 (s, 3H, —CH3), 2.42 (s, 3H, —CH3), 7.33 (d, J=8.4 Hz, 2H, Ar—H), 7.42 (d, J=8.4 Hz, 2H, Ar—H), 7.79 (d, J=8.1 Hz, 2H, Ar—H), 7.90-7.93 (m, 2H, Ar—H), 8.01 (d, J=8.1 Hz, 1H, Ar—H), 8.13-8.16 (m, 1H, Ar—H), 8.18-8.20 (m, 1H, Ar—H), 8.42 (d, J=8.7 Hz, 1H, Ar—H), 10.06 (s, 1H, Ar—NH—), 10.90 (s, 1H, Ar—NH—); 13C-NMR (300 MHz, DMSO-d6) δ (ppm): 20.37, 20.48, 125.02, 125.90, 126.61, 126.90, 127.45, 128.88, 128.92, 129.28, 129.70, 129.99, 130.39, 130.57, 131.79, 133.85, 134.00, 134.14, 138.94, 142.12, 142.20, 164.50 (NCO), 165.85 (NCO), 181.21 (CO), 183.84 (CO).

Fuente