2-Methoxyethylamine → N-(2-methoxyethyl)acrylamide

HRID 2054569Notes

Reaction equation

HRID 2054569 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].C(OCC)(=O)C.[C:12](Cl)(=[O:15])[CH:13]=[CH2:14]>C(N(CC)CC)C>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:12](=[O:15])[CH:13]=[CH2:14]

Participants

5

Procedure

2-Methoxyethylamine (44.6 g), ethyl acetate (100 mL) and triethylamine (50.6 g) were introduced into a 300 mL flask equipped with a dropping funnel and a magnetic stirrer. The flask was immersed in an ice bath and the contents of the flask were stirred as nitrogen gas was being introduced. Acryloyl chloride (45.3 g) was introduced into the dropping funnel and was added dropwise over a period of approximately one hour. After the dropwise addition was completed, stirring was continued for 1 hour at room temperature. The salt, which was separated out by suction filtration using celite, was separated by filtration, after which low boiling point components were removed with a rotary vacuum evaporator. Purification was performed by distillation under reduced pressure and N-(2-methoxyethyl)acrylamide was obtained as a colorless transparent liquid.

Workup

  1. customequipped with a dropping funnel and a magnetic stirrer
  2. customThe flask was immersed in an ice bath
  3. additionwas being introduced
  4. additionwas added dropwise over a period of approximately one hour
  5. additionAfter the dropwise addition
  6. stirringstirring
  7. customThe salt, which was separated out by suction filtration
  8. customwas separated by filtration
  9. customafter which low boiling point components were removed with a rotary vacuum evaporator
  10. customPurification
  11. distillationwas performed by distillation under reduced pressure

Sources & evidence

ORD record
ord-74344169ebee4aa3a6a217bb202ca754
Source dataset
uspto-grants-2008_02
Patent number
US07329694B2

Reaction notes

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