2-Hydroxyethyl Methacrylate → 2-Methacryloyloxyethyloxycarbonylpropyleneurea

HRID 2372503Notes

Reaction equation

HRID 2372503 reaction equation
[O:1]([C:8]([CH2:10][CH:11]([NH:13][C:14]([NH2:16])=[O:15])[CH3:12])=[O:9])[C:2]1[CH:7]=CC=CC=1.[C:17]([O:22]CCO)(=[O:21])[C:18]([CH3:20])=[CH2:19]>O1CCOCC1.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>[C:17]([O:22][CH2:7][CH2:2][O:1][C:8]([CH2:10][CH:11]([NH:13][C:14]([NH2:16])=[O:15])[CH3:12])=[O:9])(=[O:21])[C:18]([CH3:20])=[CH2:19]

Participants

5

Reactant 2

HCID 133602-Hydroxyethyl MethacrylateHCID 67742160Phenoxycarbonylpropyleneurea

Product 1

HCID 867455762-MethacryloyloxyethyloxycarbonylpropyleneureaYield 77.5%

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 312751,4-DioxaneSolvent

Procedure

One hundred gram (450 mmol) of phenoxycarbonylpropyleneurea and 59 g (450 mmol) of hydroxyehtyl methacrylate were dissolved in 900 ml of dioxane at 85° to 90° C. Then, 400 mg of dibutyltin dilaurate was added thereto and allowed to mix for 13 hours with heat. After completion of the reaction, the mixture was concentrated and recrystalized with ether to obtain 90 g of 2-methacryloyloxyethyloxycarbonylpropyleneurea (77.5% yield).

Workup

  1. additionto mix for 13 hours
  2. temperaturewith heat
  3. customAfter completion of the reaction
  4. concentrationthe mixture was concentrated
  5. customrecrystalized with ether

Sources & evidence

ORD record
ord-75a9b4198a684479a4874ece46eed177
Source dataset
uspto-grants-1992_03
Patent number
US05098949

Reaction notes

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