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

HRID 1615016ノート

反応式

HRID 1615016 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-effde3221a0f4314b165785bde558bfb
出典データセット
uspto-grants-2014_07
特許番号
US08765738B2

反応ノート

読み込み中…