Methyl iodide → Poly(oxy-1,2-ethanediyl), α-methyl-ω-[2-[(1-oxo-2-propen-1-yl)amino]ethoxy]-

HRID 2054571Notes

Reaction equation

HRID 2054571 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8](=[O:11])[CH:9]=[CH2:10].[OH-].[K+].[CH3:14]I>O1CCCC1>[CH3:14][O:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8](=[O:11])[CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 19364541HCID 19364541, compound

Product 1

HCID 61849582Poly(oxy-1,2-ethanediyl), α-methyl-ω-[2-[(1-oxo-2-propen-1-yl)amino]ethoxy]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

N-[2-(2-hydroxyethoxy)ethyl]acrylamide (35.87 g), potassium hydroxide (15.2 g), tetrahydrofuran (100 g) and methyl iodide (33.58 g) were introduced into a 1 L eggplant type flask equipped with a reflux condenser and a magnetic rotor. A reaction was carried out at 45° C. for 2 hours and then for 2 hours at 60° C. as the mixture was being stirred. The salt that separated out was removed by filtration and the low boiling point components were removed by means of a rotary vacuum evaporator. Purification was performed by distillation under reduced pressure and N-[2-(2-methoxyethoxy)ethyl]acrylamide was obtained as a yellow transparent, viscous liquid.

Workup

  1. customequipped with a reflux condenser
  2. customThe salt that separated out
  3. customwas removed by filtration
  4. customthe low boiling point components were removed by means of a rotary vacuum evaporator
  5. customPurification
  6. distillationwas performed by distillation under reduced pressure

Sources & evidence

ORD record
ord-3ed0b7e229d8429baa4f38b435f191b5
Source dataset
uspto-grants-2008_02
Patent number
US07329694B2

Reaction notes

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