Ethanolamine → Butanamide, 4-hydroxy-N-(2-hydroxyethyl)-

HRID 614087Notes

Reaction equation

HRID 614087 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5]1(=[O:10])[O:9][CH2:8][CH2:7][CH2:6]1>CO>[OH:2][CH2:1][CH2:3][NH:4][C:8](=[O:9])[CH2:7][CH2:6][CH2:5][OH:10]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 7302Gamma-Butyrolactone

Product 1

HCID 522232Butanamide, 4-hydroxy-N-(2-hydroxyethyl)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 24.4 gm (0.4 mole) of ethanolamine in 30 ml of methanol were slowly added dropwise with stirring to a solution of 34.4 gm (0.4 mole) of γ - butyrolactone in 50 ml of methanol. The temperature rose to 50° C. The mixture was subsequently heated for 3 hours at boiling and the methanol was distilled off under reduced pressure. A quantitative yield of N-(2-hydroxyethyl)-γ-hydroxybutyramide was obtained in the form of a colorless viscous liquid. The compound became crystalline after standing for a long period of time and melts at 54° to 56° C.

Workup

  1. customrose to 50° C
  2. temperatureThe mixture was subsequently heated for 3 hours
  3. distillationthe methanol was distilled off under reduced pressure

Sources & evidence

ORD record
ord-944c324581af4d9a9aeadbc00740afc3
Source dataset
uspto-grants-1979_03
Patent number
US04143159

Reaction notes

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