Ethanolamine → N-(2-hydroxyethyl)acetoacetamide

HRID 1055213Notes

Reaction equation

HRID 1055213 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[CH2:5]=[C:6]1[O:10][C:8](=[O:9])[CH2:7]1>O1CCCC1>[OH:2][CH2:1][CH2:3][NH:4][C:8](=[O:9])[CH2:7][C:6](=[O:10])[CH3:5]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 12661Diketene

Product 1

HCID 90459N-(2-hydroxyethyl)acetoacetamideYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

23 ml (0.38 mmol) of ethanolamine were added dropwise to a solution of 30 g of diketene (0.36 mol) in 300 ml tetrahydrofuran at −5 to 0° C. After 1 h stirring at 0° C. no more starting material was detected by thin layer chromatography. The reaction mixture was evaporated and the residue purified by column chromatography. This gave 41.44 g (0.29 mol, 80% yield) as a white solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-ac1ee4fcf736448f9f358f0193f81a17
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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