Triethylamine → N-(2,2-Dimethoxyethyl)methacrylamide

HRID 1080751Notes

Reaction equation

HRID 1080751 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:7][O:8][CH:9]([O:12][CH3:13])[CH2:10][NH2:11].C(N(CC)CC)C>ClCCl>[CH3:7][O:8][CH:9]([O:12][CH3:13])[CH2:10][NH:11][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Procedure

Over a period of 4 hours, 104.5 parts of methacryloyl chloride dissolved in 105 parts of dichloromethane are added dropwise at a maximum of 15° C., while cooling with ice, to 105.14 parts of aminoacetaldehyde dimethylacetal and 101.2 parts of triethylamine in 200 parts of dichloromethane. When the reaction is complete, the dichloromethane phase is washed with 200 parts of water then with 200 parts of 1N HCl solution, and then twice with 200 parts of water. After drying with anhydrous magnesium sulfate, the dichloromethane phase is concentrated by evaporation and stabilised with 0.1% of 2,6-di-tert-butyl-p-cresol, based on the reaction product. After distillation at 90° C. 10-3 mbar, 112 g of methacrylamidoacetaldehyde dimethylacetal are obtained in the form of a colourless liquid, boiling point 92° C. 10-3 mbar (65% yield).

Workup

  1. additionare added dropwise at a maximum of 15° C.
  2. washthe dichloromethane phase is washed with 200 parts of water
  3. dry with materialAfter drying with anhydrous magnesium sulfate
  4. concentrationthe dichloromethane phase is concentrated by evaporation
  5. distillationAfter distillation at 90° C

Sources & evidence

ORD record
ord-2bb3282df3c644aba31b354f6c8cafde
Source dataset
uspto-grants-1996_12
Patent number
US05583163

Reaction notes

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