Isophorone diisocyanate → Isophorone bisurethane bisethylmaleimide

HRID 23969

Reaction equation

HRID 23969 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-744b6f7830e74138ba8d3a0fa822c2b4
Source dataset
uspto-grants-2005_02
Patent number
US06855745B2

Linked notes

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