2-Ethylhexyl acrylate → HCID 54565263, compound

HRID 2291676Notes

Reaction equation

[CH:1](=[C:8]1[NH:12][C:11](=[O:13])[NH:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([O:19][CH2:20][CH:21]([CH2:26][CH3:27])[CH2:22][CH2:23][CH2:24][CH3:25])(=[O:18])[CH:16]=[CH2:17].[OH-:28].[K+]>CN(C=O)C>[CH:1](=[C:8]1[C:9](=[O:14])[N:10]([CH2:17][CH2:16][C:15]([O:19][CH2:20][CH:21]([CH2:26][CH3:27])[CH2:22][CH2:23][CH2:24][CH3:25])=[O:18])[C:11](=[O:13])[N:12]1[CH2:17][CH2:16][C:15]([O:19][CH2:20][CH:21]([CH2:26][CH3:27])[CH2:22][CH2:23][CH2:24][CH3:25])=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

10 g (53.1 mmol) of benzalhydantoin, 23.6 g (127.6 mmol) of 2-ethylhexyl acrylate and 0.6 g (10.6 mmol) of potassium hydroxide were added to 100 ml of DMF, and the mixture was stirred at 110° C. for 2 hours. After cooling, the reaction solution was extracted with ethyl acetate, and the organic layer was washed with water, dried with sodium sulfate and concentrated under reduced pressure. The residue was dissolved in toluene and crystallized by adding hexane. The crystals were filtered out and dried to obtain 19.8 g of bis(2-ethylhexyl) 4-benzylidene-2,5-dioxo-1,3-imidazolidinedipropionate (yield: 42.3%).

Workup

temperatureAfter cooling
extractionthe reaction solution was extracted with ethyl acetate
washthe organic layer was washed with water
dry with materialdried with sodium sulfate
concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in toluene
customcrystallized
additionby adding hexane
filtrationThe crystals were filtered out
customdried

Sources & evidence

ORD record: ord-b08cd7b83a984d839233bcf5fbedb213
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04797493

Reaction notes

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