Diethanolamine → N,N-Bis(2-hydroxyethyl)-3-oxobutanamide

HRID 1055187Notes

Reaction equation

HRID 1055187 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].[CH2:8]=[C:9]1[O:13][C:11](=[O:12])[CH2:10]1>CO>[OH:4][CH2:3][CH2:2][N:1]([CH2:5][CH2:6][OH:7])[C:11](=[O:12])[CH2:10][C:9](=[O:13])[CH3:8]

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 12661Diketene

Product 1

HCID 21553722N,N-Bis(2-hydroxyethyl)-3-oxobutanamideYield 90.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 52.53 g (0.50 mol) diethanolamine in 100 ml MeOH was added dropwise to a solution of 40.00 g (0.48) diketene in 100 ml MeOH at 0° C. After stirring for 1 hour at 0° C., no starting material was detected anymore by thin-layer chromatography. The reaction mixture was spun off and the residue was purified by means of column chromatography. 81.32 g of product was obtained as a slightly yellow oil.

Workup

  1. customthe residue was purified by means of column chromatography

Sources & evidence

ORD record
ord-6c2d8a4774964feb9ffd672aa3f9189d
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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