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Chlorine monoxide → (+/-)-cis-8,9-Dimethoxy-6-[4-(methoxycarbonyl)phenyl]-1,2,3,4,4a,10b-hexahydrophenanthridine

HRID 635822
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HRID 635822 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[NH:17][C:18](=O)[C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O(Cl)Cl.C(=O)(O)[O-].[Na+]>C(#N)C>[CH3:10][O:9][C:8]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[C@H:11]1[C@H:12]([CH2:13][CH2:14][CH2:15][CH2:16]1)[N:17]=[C:18]2[C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=1
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참가 물질

5

반응물 3

HCID 24646Chlorine monoxideHCID 516892Sodium BicarbonateHCID 53911096(+/-)-cis-n-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-4-methoxycarbonylbenzamide

생성물 1

HCID 70021069(+/-)-cis-8,9-Dimethoxy-6-[4-(methoxycarbonyl)phenyl]-1,2,3,4,4a,10b-hexahydrophenanthridine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1.8 g of (+/−)-cis-N-[2-(3,4-dimethoxyphenyl)cyclohexyl]-4-methoxycarbonylbenzamide are dissolved in 50 ml of acetonitrile and 1.0 ml of phoshorus oxychloride and stirred at 50° C. for 8 h. The reaction mixture is poured into 100 ml of saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic phase is washed with sodium bicarbonate solution and water, dried with sodium sulfate and concentrated. The residue is recrystallized from ethyl acetate/petroleum ether. This gives 660 mg (38.6% of Th.) of the title compound of m.p.: 121.5-122.5° C.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with sodium bicarbonate solution and water
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is recrystallized from ethyl acetate/petroleum ether

출처 및 근거

ORD 기록
ord-2732bf4ca39f4108845e810d14ad117f
출처 데이터셋
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06191138B1

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