Reaction #52247

Reaction equation

Hydroxy ethylmaleimide

isophorone diisocyanate

→

Isophorone Bisurethane Bisethylmaleimide

Solvents

acetone

Conditions

Workup

1. 1
   Otherpurged with nitrogen
2. 2
   workup.ADDITIONOne drop of dibutyl tin dilaurate was added to the solution
3. 3
   workup.STIRRINGto stir overnight
4. 4
   Othera white precipitate was obtained
5. 5
   Otherafter solvent removal m.p. 105-112° C. (40.5 g, 100%)

Procedure

Hydroxy ethylmaleimide (10 g, 0.141 mol) was dissolved in acetone and purged with nitrogen while stirring in an ice bath. One drop of dibutyl tin dilaurate was added to the solution. The isophorone diisocyanate (30.5 g, 0.141 mol) was added dropwise over 2-3 hours. The solution was allowed to stir overnight and a white precipitate was obtained after solvent removal m.p. 105-112° C. (40.5 g, 100%). 1H-NMR (D6-DMSO, δ, ppm): 3.63-3.58 (2H, —NCH2—), 4.08-4.03 (2H, —CH2O—, t), 7.03 (2H, —CH═CH—, s). 13C-NMR (D6-DMSO, δ, ppm): 134.5 (2C, —CH═CH—), 154.9 (2C, NHC═O), (170.7 (2C, —NC═O).

Source