1,4-Dioxane → 2-(p-Vinylphenyl)ethyloxycarbonylpropyleneurea

HRID 1646324Notes

Reaction equation

HRID 1646324 reaction equation
[O:1]([C:8]([CH2:10][CH:11]([NH:13][C:14]([NH2:16])=[O:15])[CH3:12])=[O:9])C1C=CC=CC=1.OCC[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O1CCO[CH2:30][CH2:29]1>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>[CH:29]([C:25]1[CH:24]=[CH:23][C:22]([CH2:21][CH2:20][O:9][C:8]([CH2:10][CH:11]([NH:13][C:14]([NH2:16])=[O:15])[CH3:12])=[O:1])=[CH:27][CH:26]=1)=[CH2:30]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 576060HydroxyethylstyreneHCID 67742160Phenoxycarbonylpropyleneurea

Product 1

HCID 677852952-(p-Vinylphenyl)ethyloxycarbonylpropyleneureaYield 40%

Reagents, catalysts & solvents 1

HCID 9809426Di-n-butyldilauryltinCatalyst

Procedure

Phenoxycarbonylpropyleneurea 8.2 g (37.3 mmol) and hydroxyethylstyrene 5 g (37.3 mmol) were dissolved into dioxane 90 ml by heating. Into the solution obtained was added dibutyltin dilaurate 0.5 g, and the mixture was heated for 6 hours with stirring. After the reaction the solution was concentrated to give a solid mass, which was then purified by column chromatography. The title compound 3.9 g (yield: 40%) was obtained, which was analyzed and showed:

Workup

  1. temperatureby heating
  2. customInto the solution obtained
  3. temperaturethe mixture was heated for 6 hours
  4. customAfter the reaction the solution
  5. concentrationwas concentrated
  6. customto give a solid mass, which
  7. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-8b5699bef3a444d4a6ad1993e65c4294
Source dataset
uspto-grants-1993_01
Patent number
US05179184

Reaction notes

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