Dimethylformamide → HCID 53987253, compound

HRID 2291674Notes

Reaction equation

HRID 2291674 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

6

Reactant 4

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

Product 1

HCID 53987253HCID 53987253, compoundYield 77.8%

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. 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

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

Sources & evidence

ORD record
ord-0bdd8a8dece64b5d853038319b4c7b9b
Source dataset
uspto-grants-1989_01
Patent number
US04797493

Reaction notes

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