Dimethylformamide → HCID 53987253, compound

HRID 703761Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1OC)[CH:6]=[C:7]1[NH:11][C:10](=[O:12])[NH:9][C:8]1=[O:13].[C:19]([O:23][CH2:24][CH:25]([CH2:30][CH3:31])[CH2:26][CH2:27][CH2:28][CH3:29])(=[O:22])[CH:20]=[CH2:21].[OH-].[K+].CN(C)[CH:36]=[O:37]>O>[CH3:36][O:37][C:4]1[C:3]([O:2][CH3:1])=[CH:16][CH:15]=[CH:14][C:5]=1[CH:6]=[C:7]1[C:8](=[O:13])[N:9]([CH2:21][CH2:20][C:19]([O:23][CH2:24][CH:25]([CH2:30][CH3:31])[CH2:26][CH2:27][CH2:28][CH3:29])=[O:22])[C:10](=[O:12])[NH:11]1

Participants

Conditions

Temperature: 110 °C

Procedure

20 g (80.6 mmol) of 5-(3,4-dimethoxybenzylidene)-hydantoin, 17.8 g (96 mmol) of 2-ethylhexyl acrylate and 0.90 g (1.6 mmol) of potassium hydroxide were added to 150 ml of dimethylformamide, and the mixture was stirred at 110° C. for 2 hours. After cooling, the reaction solution was added with 200 ml of water and extracted with 500 ml of ethyl acetate. The extract was dried with sodium sulfate and then the solvent was distilled off under reduced pressure. The residue was recrystallized with toluene-n-hexane (1:1) and the precipitated crystals were dried to obtain 27.1 g of 2-ethylhexyl 4-(2,3-dimethoxyphenylmethylene)-2,5-dioxo-1-imidazolidinepropionate (yield: 77.8 %).

Workup

temperatureAfter cooling
extractionextracted with 500 ml of ethyl acetate
dry with materialThe extract was dried with sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was recrystallized with toluene-n-hexane (1:1)
customthe precipitated crystals were dried

Sources & evidence

ORD record: ord-02306b9503f44580b618e56d09edba19
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04985237

Reaction notes

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