반응 #69056

반응 방정식

DIPEA

thiomorpholine

ethyl acetate

CC-12

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

→

1-(4-methylbenzamido)-2-[2-(1,4-thiazinan-4-yl)acetylamino]-anthraquinone

수율 51.0%

용매

EtOH

n-hexane

tetrahydrofuran

반응 조건

후처리

1. 1
   온도This mixture was heated
2. 2
   온도under reflux for 16 hours
3. 3
   기타After the completion of the reaction
4. 4
   여과the mixture was filtered
5. 5
   농축the filtrate was concentrated by reduced pressure concentrator (such as Vacuum Evaporator)
6. 6
   추출The residue was extracted with ethyl acetate for several times
7. 7
   기타The extract was dried on magnesium sulfate
8. 8
   농축concentrated under reduced pressure
9. 9
   세척The crude product was washed with ethyl acetate/hexane
10. 10
    기타Finally, the crude product was recrystallized in hot ethanol
11. 11
    기타to obtain a kelly green compound CC-42

실험 절차

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 thiomorpholine (0.80 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-42. Mol. Wt.: 499.5808 (C28H25N3O4S); Rf: 0.43 (ethyl acetate:n-hexane=1:2); Yield: 51%; Mp.: 210-211° C. (EtOH); HRMS (EI) m/z: calcd [M]+, 499.1566 (C28H25N3O4S+). Found, 499.1570. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 2:39 (br, 4H, —CH2—), 2.45 (s, 3H, —CH3), 3.15 (s, 2H, —CH2N—), 3.23 (br, 4H, —CH2—), 7.45 (d, J=8.1 Hz, 2H, Ar—H), 7.88-7.91 (m, 2H, Ar—H), 8.07-8.19 (m, 4H, Ar—H), 8.27 (d, J=8.4 Hz, 1H, Ar—H), 8.73 (d, J=8.4 Hz, 1H, Ar—H), 10.00 (s, 1H, Ar—NH—), 10.61 (s, 1H, Ar—NH—); 13C-NMR (75 MHz, DMSO-d6) δ (ppm): 20.89, 26.48, 53.13, 54.62, 61.92, 65.54, 127.72, 126.30, 126.40, 126.92, 127.69, 127.92, 127.98, 129.22, 129.43, 130.53, 132.30, 134.12, 134.41, 134.45, 140.21, 142.61, 166.27 (NCO), 168.89, 169.15 (NCO), 181.42 (CO), 183.84 (CO).

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