Ethanolamine → N-(2-hydroxyethyl)acetoacetamide

HRID 326971Notes

Reaction equation

HRID 326971 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[CH2:7]([CH2:9][NH2:10])[OH:8].O>ClCCl>[OH:8][CH2:7][CH2:9][NH:10][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 962WaterHCID 12661Diketene

Product 1

HCID 90459N-(2-hydroxyethyl)acetoacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diketene (42.1 g, 0.5 mol) in dichloromethane (100 ml), ethanolamine (30.5 g, 0.5 mol) was added dropwise at 10°-20.C with stirring, and the reaction was carried out at room temperature for 2 hrs. After pouring H2O (200 ml) into the reaction solution, an aqueous layer was separated, washed thrice with dichloromethane and was obtained N-(2-hydroxyethyl)-3-oxobutanamide as an aqueous solution.

Workup

  1. customan aqueous layer was separated
  2. washwashed thrice with dichloromethane

Sources & evidence

ORD record
ord-55e6ecaea3874d09a62fadad20f56bd4
Source dataset
uspto-grants-1993_12
Patent number
US05272036

Reaction notes

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