N-3-Bromopropylphthalimide → N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-N-isopropyl-2-nitrobenzenesulfonamide

HRID 1893497Notes

Reaction equation

HRID 1893497 reaction equation
[CH:1]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])(=[O:7])=[O:6])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:20][CH2:21][CH2:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33]>CN1CCCC1=O.C(OCC)(=O)C>[O:33]=[C:24]1[C:25]2[C:26](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](=[O:28])[N:23]1[CH2:22][CH2:21][CH2:20][N:4]([CH:1]([CH3:3])[CH3:2])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])(=[O:7])=[O:6]

Participants

6

Reactant 3

HCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 4154456N-isopropyl-2-nitrobenzenesulfonamide

Product 1

HCID 66880021N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-N-isopropyl-2-nitrobenzenesulfonamideYield 73%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The compound (6.29 g, 25.75 mmol) obtained in step A was dissolved in N-methylpyrrolidone (100 ml), and the mixture was stirred under ice-cooling. Thereto was added 60% sodium hydride (1.21 g, 30 mmol) and the mixture was stirred at room temperature for 20 min. After stirring, N-(3-bromopropyl)phthalimide (8.31 g, 31.0 mmol) was added and the mixture was stirred at 70° C. for 90 min. The reaction mixture was diluted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained solid was washed with diethyl ether-hexane mixed solvent, and dried under reduced pressure to give the title compound (8.11 g, yield 73%) as a colorless solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 20 min
  3. stirringAfter stirring
  4. stirringthe mixture was stirred at 70° C. for 90 min
  5. washwashed with water, saturated aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe solution was concentrated under reduced pressure
  9. washThe obtained solid was washed with diethyl ether-hexane mixed solvent
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-75e9957dcbb74f12bc3d441f1317541e
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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