Isophorone diisocyanate → Isophorone bisurethane bisethylmaleimide

HRID 840802Notes

Reaction equation

HRID 840802 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:5]([NH:7][C:8](=[O:10])[CH:9]=1)=[O:6].[O:11]=[C:12]=[N:13][CH:14]1[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:16](C)([CH2:17]N=C=O)[CH2:15]1>CC(C)=O>[CH2:3]([C:4]1[C:5](=[O:6])[NH:7][C:8](=[O:10])[C:9]=1[CH2:14][CH3:15])[CH3:2].[NH2:13][C:12]([O:10][CH2:8][CH3:9])=[O:11].[NH2:13][C:12]([O:10][CH2:8][CH3:9])=[O:11].[O:1]=[C:14]1[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:16]([CH3:17])=[CH:15]1

Participants

4

Reactant 2

HCID 169132Isophorone diisocyanateHCID 22337974Hydroxy ethylmaleimide

Product 1

HCID 86584361Isophorone bisurethane bisethylmaleimide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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).

Workup

  1. custompurged with nitrogen
  2. additionOne drop of dibutyl tin dilaurate was added to the solution
  3. stirringto stir overnight
  4. customa white precipitate was obtained
  5. customafter solvent removal m.p. 105-112° C. (40.5 g, 100%)

Sources & evidence

ORD record
ord-70f566f0e68444018f23370d5b8cef3b
Source dataset
uspto-grants-2002_04
Patent number
US06369124B1

Reaction notes

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