Phenyl isocyanate → Ethyl-beta-phenylureido-beta-ethoxy acrylate

HRID 1449072Notes

Reaction equation

HRID 1449072 reaction equation
[C:1]([O:5][O:6][C:7]([CH2:10][CH3:11])([NH2:9])[CH3:8])(=[O:4])[CH:2]=[CH2:3].[C:12]1([N:18]=[C:19]=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(#N)C>[C:1]([O:5][O:6][C:7]([CH2:10][CH3:11])([NH:9][C:19]([NH:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:20])[CH3:8])(=[O:4])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 86736826Ethylbeta-amino-beta-ethoxy acrylate

Product 1

HCID 86736828Ethyl-beta-phenylureido-beta-ethoxy acrylateYield 43.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a solution of 15.9 g of ethyl-β-amino-β-ethoxy acrylate in 30 ml of acetonitrile there was dropped 11.9 g of phenyl isocyanate while cooling, and the resulting mixture was allowed to stand at room temperature for 5 hours. The acetonitrile was then distilled away. To the residue was added 100 ml of ether, which was then dried over anhydrous sodium sulfate. The ether was distilled away and the residue obtained was distilled under reduced pressure. Thus, 12 g of ethyl-β-phenylureido-β-ethoxy acrylate of a boiling point of 83° to 84° C./0.5 mmHg was obtained.

Workup

  1. temperaturewhile cooling
  2. distillationThe acetonitrile was then distilled away
  3. additionTo the residue was added 100 ml of ether, which
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. distillationThe ether was distilled away
  6. customthe residue obtained
  7. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-b29fea7f74284a7ea5005b5f90590028
Source dataset
uspto-grants-1980_02
Patent number
US04188489

Reaction notes

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