Divinyl sulfone → HCID 59827394, compound
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- stirringSubsequently, the mixture was stirred at 40-50° C. for 3 more hours
- stirringAfter stopping stirring
- temperaturethe reaction solution was cooled to room temperature
- customprecipitated
- additiondispersed in 100 mL of methanol
- filtrationThe resultant precipitate was filtered
- additionredispersed in a large volume of clean water
- filtrationfiltered again
- washwashed
- customto remove salt
- additionThen, the product was redispersed in 50 mL of methanol
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-834772eb6ae5405d81e43b450846fa3f
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362276B2
Reaction notes
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