1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → HCID 53817008, compound

HRID 343797Notes

Reaction equation

HRID 343797 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].[Cl:15][C:16]1[C:17]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[C:18]2[C:23](=[CH:24][C:25]=1[Cl:26])[N:22]=[C:21]([O:27][CH3:28])[C:20]([O:29][CH3:30])=[N:19]2.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:15][C:16]1[C:17]([N:31]([CH2:2][CH2:3][N:4]2[C:8](=[O:9])[C:7]3=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]3[C:5]2=[O:14])[S:32]([CH3:35])(=[O:34])=[O:33])=[C:18]2[C:23](=[CH:24][C:25]=1[Cl:26])[N:22]=[C:21]([O:27][CH3:28])[C:20]([O:29][CH3:30])=[N:19]2

Participants

5

Reactant 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-2×HCID 11430Potassium CarbonateHCID 54321377HCID 54321377, compound

Product 1

HCID 53817008HCID 53817008, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-(2-bromoethyl)phthalimide (1.73 g, 6.81 mmol) was added to a refluxing mixture of N-(6,7-dichloro-2,3-dimethoxy-quinoxalin-5-yl)-methanesulphonamide (2.00 g, 5.68 mmol) and potassium carbonate (1.88 g, 13.63 mmol) in acetone (100 ml) under nitrogen. After 48 hours, further N-(2-bromoethyl)phthalimide (1.73 g, 6.81 mmol) was added and refluxing continued for 18 hours. After cooling the mixture was concentrated under reduced pressure and the residue dissolved in dichloromethane. The resulting solution was washed twice with 1N sodium hydroxide solution, water and brine and then dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with hexane:ethyl acetate) to afford N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(2-phthalimidoethyl)methanesulphonamide as a pale yellow solid (2.55 g, 85%).

Workup

  1. temperaturerefluxing
  2. waitcontinued for 18 hours
  3. temperatureAfter cooling the mixture
  4. concentrationwas concentrated under reduced pressure
  5. dissolutionthe residue dissolved in dichloromethane
  6. washThe resulting solution was washed twice with 1N sodium hydroxide solution, water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (eluting with hexane:ethyl acetate)

Sources & evidence

ORD record
ord-a51d0298a7914526b62e8b65b9dcd8d1
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

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