Dimethylamine → Ethyl 2-dimethylaminomethylacrylate

HRID 616429Notes

Reaction equation

HRID 616429 reaction equation
[CH2:1]=O.[C:3]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:4][C:5]([O-])=O.[K+].[CH3:13][NH:14][CH3:15]>O>[CH3:13][N:14]([CH2:5][C:4](=[CH2:1])[C:3]([O:9][CH2:10][CH3:11])=[O:8])[CH3:15]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 3446434Potassium ethyl malonate

Product 1

HCID 20370247Ethyl 2-dimethylaminomethylacrylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Formaldehyde (60 ml of 40% solution) was added to a stirred solution of potassium ethyl malonate (34g) and dimethylamine (40 ml of 26% solution) in water (100 ml) at 15° C. The solution was stirred at laboratory temperature for one hour and then boiled under reflux for one hour. After cooling the solution was extracted with ether and the ether was evaporated to leave the product as a yellow oil. This was distilled to give a clear oil (boiling point 84° C/20 mm).

Workup

  1. temperatureunder reflux for one hour
  2. temperatureAfter cooling the solution
  3. extractionwas extracted with ether
  4. customthe ether was evaporated

Sources & evidence

ORD record
ord-056f3d710dee46f49a7fd54ed0f847ad
Source dataset
uspto-grants-1978_02
Patent number
US04074051

Reaction notes

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