Sodium hydride → 2-Nitro-N-[3-(3-oxo-2,3-dihydrocyclopenta[c]carbazol-6(1H)-yl)propyl]-N-propylbenzenesulfonamide

HRID 1615016노트

반응식

HRID 1615016 반응식
[CH2:1]1[C:16]2[C:15]3[C:14]4[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=4[NH:8][C:7]=3[CH:6]=[CH:5][C:4]=2[C:3](=[O:17])[CH2:2]1.Br[CH2:19][CH2:20][CH2:21][N:22]([CH2:35][CH2:36][CH3:37])[S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N+:32]([O-:34])=[O:33])(=[O:25])=[O:24].[H-].[Na+].CCCCCC.C(OCC)(=O)C>C(Cl)Cl>[N+:32]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[S:23]([N:22]([CH2:35][CH2:36][CH2:37][N:8]1[C:7]2[CH:6]=[CH:5][C:4]3[C:3](=[O:17])[CH2:2][CH2:1][C:16]=3[C:15]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)[CH2:21][CH2:20][CH3:19])(=[O:25])=[O:24])([O-:34])=[O:33]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 21226206Ethyl acetate hexaneHCID 585448961,6-Dihydrocyclopenta[c]carbazol-3(2H)-oneHCID 67368759N-(3-bromopropyl)-2-nitro-N-propylbenzenesulfonamide

생성물 1

HCID 673779462-Nitro-N-[3-(3-oxo-2,3-dihydrocyclopenta[c]carbazol-6(1H)-yl)propyl]-N-propylbenzenesulfonamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Compound 46 (0.538 g, 2.43 mmol) and bromide 50 (0.9 g, 2.46 mmol) were dissolved in CH2Cl2 (30 mL). Then NaH (0.15 g, 3.75 mmol, 1.5 eq.) was added. The reaction mixture was stirred for 20 min (TLC monitoring, eluent: hexane-ethyl acetate, 1:1). Then, the mixture was poured onto ice. The product was extracted with ethyl acetate, and the extract was evaporated in a rotary evaporator. The residue of CH2Cl2 was removed in high vacuum. Methanol was added to the hardened precipitate. The product was triturated; the precipitate was filtered off. Yield of 47: 0.638 g (52%).

후처리

  1. additionThen, the mixture was poured onto ice
  2. extractionThe product was extracted with ethyl acetate
  3. customthe extract was evaporated in a rotary evaporator
  4. customThe residue of CH2Cl2 was removed in high vacuum
  5. additionMethanol was added to the hardened precipitate
  6. customThe product was triturated
  7. filtrationthe precipitate was filtered off

출처 및 근거

ORD 기록
ord-effde3221a0f4314b165785bde558bfb
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765738B2

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