Ethyl isocyanate → Ethyl-beta-ethylureido-beta-ethoxy acrylate

HRID 1449071Notes

Reaction equation

HRID 1449071 reaction equation
[C:1]([O:5][O:6][C:7]([CH2:10][CH3:11])([NH2:9])[CH3:8])(=[O:4])[CH:2]=[CH2:3].[CH2:12]([N:14]=[C:15]=[O:16])[CH3:13]>C(#N)C>[C:1]([O:5][O:6][C:7]([CH2:10][CH3:11])([NH:9][C:15]([NH:14][CH2:12][CH3:13])=[O:16])[CH3:8])(=[O:4])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 86736826Ethylbeta-amino-beta-ethoxy acrylate

Product 1

HCID 86736827Ethyl-beta-ethylureido-beta-ethoxy acrylateYield 60.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 15.9 g of ethyl-β-amino-β-ethoxy acrylate in 30 ml of acetonitrile was added 7.1 g of ethyl isocyanate, and the resulting mixture was allowed to stand at room temperature for one day and one night. The acetonitrile was distilled away under reduced pressure. To the residue was added 100 ml of ether and the system then dried over anhydrous sodium sulfate. The ether was distilled away and the residue was distilled under reduced pressure. Thus, 14 g of ethyl-β-ethylureido-β-ethoxy acrylate of a boiling point of 127° to 130° C. was obtained.

Workup

  1. distillationThe acetonitrile was distilled away under reduced pressure
  2. additionTo the residue was added 100 ml of ether
  3. dry with materialthe system then dried over anhydrous sodium sulfate
  4. distillationThe ether was distilled away
  5. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-b7874db0e41f449080b95e1129020dc2
Source dataset
uspto-grants-1980_02
Patent number
US04188489

Reaction notes

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