Succinimide → HCID 59827395, compound

HRID 1811370Notes

Reaction equation

HRID 1811370 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH2:3][CH2:2]1.[CH:8]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])=[CH2:9].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCOCC1>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([S:10]([CH2:8][CH2:9][N:5]2[C:4](=[O:6])[CH2:3][CH2:2][C:1]2=[O:7])(=[O:12])=[O:11])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 11439SuccinimideHCID 3056334-ethenesulfonylphenylamineHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 59827395HCID 59827395, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

In a 100 mL round bottom flask, a mixture of 1.15 g of succinimide, 2 g of 4-ethenesulfonylphenylamine and 30 g of 1,4-dioxane was heated to 60-70° C. and stirred. To the reaction solution was added 0.75 g of 40% aqueous tetrabutylammonium hydroxide solution 3 times over a 1-hour period. Subsequently, the mixture was stirred at 60-70° C. for 2 more hours. When the solution turned into a white suspension, stirring was stopped and the reaction solution was cooled to room temperature and precipitated and dispersed in 100 mL of methanol. The resultant precipitate was filtered, redispersed in 100 mL of clean water, filtered again and washed to remove salt. Then, the product was redispersed in 500 mL of methanol, filtered and dried to obtain 2.2 g of 1-[2-(4-amino-benzenesulfonyl)-ethyl]-pyrrolidine-2,5-dione (yield=70%).

Workup

  1. stirringSubsequently, the mixture was stirred at 60-70° C. for 2 more hours
  2. stirringstirring
  3. temperaturethe reaction solution was cooled to room temperature
  4. customprecipitated
  5. additiondispersed in 100 mL of methanol
  6. filtrationThe resultant precipitate was filtered
  7. additionredispersed in 100 mL of clean water
  8. filtrationfiltered again
  9. washwashed
  10. customto remove salt
  11. additionThen, the product was redispersed in 500 mL of methanol
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-fc65906575324a60927c2c74443aa77f
Source dataset
uspto-grants-2013_01
Patent number
US08362276B2

Reaction notes

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