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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1523713Generated: October 29, 2026

(S)-(+)-N-(2,3-Epoxypropyl)phthalimide → 2-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]isoindole-1,3-dione

https://huagongshe.com/reaction/1523713

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(S)-(+)-N-(2,3-Epoxypropyl)phthalimideHCID 719412—
Reactant4-(4-Isocyanatophenyl)morpholin-3-oneHCID 53341421—
CatalystTetrabutylammonium BromideHCID 74236—
SolventAcetonitrileHCID 6342—
Product2-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]isoindole-1,3-dioneHCID 1169031790%

Reaction Steps

(S)-2-(oxiran-2-ylmethy)isoindoline-1,3-dione (3.87 g, 19.06 mmol, 1.1 eq.) and 4-(4-isocyanatophenyl)morpholin-3-one (3.77 g, 17.29 mmol) were dissolved in acetonitrile (70 mL) respectively, then heated to reflux. Tetra-n-butylammonium bromide (0.55 g, 1.71 mmol) was added, the mixture was reacted for 4 h, white solid was obtained by filtration (6.57 g, yield: 90.0%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09079892B2
Source datasetuspto-grants-2015_07
ORD IDord-128d206e843f4685ab777eda8bb17e87
Source noteuspto-grants-2015_07