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

HRID 1615016Notes

Reaction equation

HRID 1615016 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-effde3221a0f4314b165785bde558bfb
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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