Divinyl sulfone → HCID 59827394, compound

HRID 1811371Notes

Reaction equation

HRID 1811371 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH:3]=[CH:2]1.[CH:8]([S:10]([CH:13]=[CH2:14])(=[O:12])=[O:11])=[CH2:9].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCOCC1>[CH:8]([S:10]([CH2:13][CH2:14][N:5]1[C:4](=[O:6])[CH:3]=[CH:2][C:1]1=[O:7])(=[O:12])=[O:11])=[CH2:9]

Participants

5

Conditions

Temperature
45 °C

Procedure

In a 50 mL round bottom flask, a mixture of 0.5 g of maleimide, 0.61 g of divinylsulfone and 10 g of 1,4-dioxane was heated to 40-50° C. and stirred. To the reaction solution was added 0.67 g of 40% aqueous tetrabutylammonium hydroxide solution. Subsequently, the mixture was stirred at 40-50° C. for 3 more hours. After stopping stirring, the reaction solution was cooled to room temperature and precipitated and dispersed in 100 mL of methanol. The resultant precipitate was filtered, redispersed in a large volume of clean water, filtered again and washed to remove salt. Then, the product was redispersed in 50 mL of methanol, filtered and dried to obtain 0.94 g of N-vinylsulfonylethylmaleimide (yield=61%)

Workup

  1. stirringSubsequently, the mixture was stirred at 40-50° C. for 3 more hours
  2. stirringAfter stopping stirring
  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 a large volume of clean water
  8. filtrationfiltered again
  9. washwashed
  10. customto remove salt
  11. additionThen, the product was redispersed in 50 mL of methanol
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-834772eb6ae5405d81e43b450846fa3f
Source dataset
uspto-grants-2013_01
Patent number
US08362276B2

Reaction notes

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