Ethanolamine → HCID 12253017, compound

HRID 542333Notes

Reaction equation

HRID 542333 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[CH2:5]([O:7][C:8](=[O:14])[C:9](OCC)=[O:10])[CH3:6]>C(Cl)Cl>[OH:2][CH2:1][CH2:3][NH:4][C:9](=[O:10])[C:8]([O:7][CH2:5][CH3:6])=[O:14]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 7268Diethyl Oxalate

Product 1

HCID 12253017HCID 12253017, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

To a mixture of 500 parts ethanolamine in methylene chloride (900 ml), cooled to -70° C., was added dropwise 2405 parts diethyloxalate. After stirring at room temperature for 16 hours, the mixture was filtered, concentrated and purified by chromatography to yield pure ethyl 2-hydroxyethyloxamate. A mixture of the oxamate (77 parts), sodium carbonate (50.2 parts) and an inhibitor in chloroform were cooled to 0° C. and acryloylchloride (43.3 parts) was added dropwise. After stirring at 0° C. for 2 hours and room temperature for 3 hours the mixture was filtered to yield 1011 parts crude ethyl N-2-ethyloxamatoacrylate.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-8930aa94608b4e7c9037a1967541ea32
Source dataset
uspto-grants-1987_04
Patent number
US04656308

Reaction notes

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