Ethanol → Ethoxycarbonylpropyleneurea

HRID 1770293Notes

Reaction equation

HRID 1770293 reaction equation
[O:1]([C:8]([CH2:10][CH:11]([NH:13][C:14]([NH2:16])=[O:15])[CH3:12])=[O:9])[C:2]1C=CC=C[CH:3]=1.C(O)C.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>O1CCOCC1>[CH2:2]([O:1][C:8]([CH2:10][CH:11]([NH:13][C:14]([NH2:16])=[O:15])[CH3:12])=[O:9])[CH3:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 9809426Di-n-butyldilauryltinHCID 67742160Phenoxycarbonylpropyleneurea

Product 1

HCID 86748426Ethoxycarbonylpropyleneurea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenoxycarbonylpropyleneurea of 1 g (4.5 mmol) and ethanol of 10 g (21.7 mmol) were dissolved in dioxane of 20 ml by heating. Dibutyltin dilaurate of 10 mg (1%) was added to the resulting solution and the resulting mixture was heated for 5 hours with stirring. After confirming the completion of the reaction by the thin layer chromatography, the reaction product was concentrated and the resulting crude crystals were washed with ether to obtain the aimed substance of 567 mg (80%).

Workup

  1. temperatureby heating
  2. temperaturethe resulting mixture was heated for 5 hours
  3. customthe completion of the reaction by the thin layer chromatography
  4. concentrationthe reaction product was concentrated
  5. washthe resulting crude crystals were washed with ether
  6. customto obtain the aimed substance of 567 mg (80%)

Sources & evidence

ORD record
ord-158e7b3fdb944bb99035cafc6a3d4f05
Source dataset
uspto-grants-1995_01
Patent number
US05385985

Reaction notes

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