Dimethylformamide → 2-Ethylhexyl 4-(3,4-dimethoxyphenylmethylene)-2,5-dioxo-1-imidazolidinepropionate

HRID 1534165Notes

Reaction equation

HRID 1534165 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[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)C=O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]2[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]2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 76362-Ethylhexyl acrylateHCID 14797Potassium HydroxideHCID 1657985-[(3,4-Dimethoxyphenyl)methylidene]imidazolidine-2,4-dione

Product 1

HCID 544095212-Ethylhexyl 4-(3,4-dimethoxyphenylmethylene)-2,5-dioxo-1-imidazolidinepropionate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with 500 ml of ethyl acetate

Sources & evidence

ORD record
ord-79c3938a860a4f3585d93b93e6c06818
Source dataset
uspto-grants-1992_02
Patent number
US05087729

Reaction notes

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