Dimethylamine → 2-((Dimethylamino)methyl)prop-2-enoic acid

HRID 616427Notes

Reaction equation

HRID 616427 reaction equation
[CH2:1]=O.[CH3:3][NH:4][CH3:5].[C:6](O)(=O)[CH2:7][C:8]([OH:10])=[O:9]>O>[CH3:3][N:4]([CH2:1][C:7](=[CH2:6])[C:8]([OH:10])=[O:9])[CH3:5]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 867Malonic Acid

Product 1

HCID 2235812-((Dimethylamino)methyl)prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Formaldehyde solution (150 ml of 40% solution) was added with stirring to a solution of dimethylamine (218g of 26% solution) and malonic acid (104g) in water (250 ml). The reaction temperature was kept at 20° C during the addition and for a further 2 hours. The solution was then heated on a steam bath for 2 hours and the water was removed under reduced pressure to give a pale yellow syrup which was dried further by azeotropic distillation with benzene.

Workup

  1. additionThe reaction temperature was kept at 20° C during the addition and for a further 2 hours
  2. temperatureThe solution was then heated on a steam bath for 2 hours
  3. customthe water was removed under reduced pressure
  4. customto give a pale yellow syrup which
  5. dry with materialwas dried further by azeotropic distillation with benzene

Sources & evidence

ORD record
ord-3c7f2cd4418e4738acdb002725855a63
Source dataset
uspto-grants-1978_02
Patent number
US04074051

Reaction notes

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