Isophorone diisocyanate → Isophorone bisurethane bisethylmaleimide

HRID 1268092Notes

Reaction equation

HRID 1268092 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-9d4d89a23cc84725a1044a12d5bb4d82
Source dataset
uspto-grants-2003_04
Patent number
US06555593B1

Reaction notes

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