Ethyl vinyl ether → 1-Methyl-4-ethoxy-2-azetidinone

HRID 2187084Notes

Reaction equation

HRID 2187084 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[CH:5]([O:7][CH2:8][CH3:9])=[CH2:6]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH:5]([O:7][CH2:8][CH3:9])[CH2:6][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 8023Ethyl vinyl etherHCID 12228Methyl Isocyanate

Product 1

HCID 152524911-Methyl-4-ethoxy-2-azetidinoneYield 16%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

A Teflon tube containing a mixture of 0.16 g (2.8 mmoles) of methyl isocyanate, 0.27 g (3.8 mmoles) of ethyl vinyl ether and 2 ml of toluene was sealed and introduced into a high-pressure reactor and the mixture was heated at 130° C. under a pressure of 8000 atmospheres for 20 hours. The reaction mixture taken out was evaporated and then purified by distillation under reduced pressure to obtain 1-methyl-4-ethoxy-2-azetidinone in a yield of 16% of the theoretical value.

Workup

  1. additionA Teflon tube containing
  2. customwas sealed
  3. additionintroduced into a high-pressure reactor
  4. customThe reaction mixture taken out was evaporated
  5. distillationpurified by distillation under reduced pressure

Sources & evidence

ORD record
ord-eda846f2fbf047dea96db40f2dd894d4
Source dataset
uspto-grants-2002_06
Patent number
US06407228B1

Reaction notes

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