Dibutylamine → n,n-dibutyl-3-oxobutanamide

HRID 400204Notes

Reaction equation

HRID 400204 reaction equation
[C:1]([O:7]CC)(=O)[CH2:2][C:3]([CH3:5])=[O:4].[CH2:10]([NH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH3:13]>C(OCC)C>[CH2:10]([N:14]([CH2:15][CH2:16][CH2:17][CH3:18])[C:1](=[O:7])[CH2:2][C:3](=[O:4])[CH3:5])[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 8148DibutylamineHCID 8868Ethyl Acetoacetate

Product 1

HCID 243714n,n-dibutyl-3-oxobutanamideYield 67.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
150 °C

Procedure

A! A mixture of ethyl acetoacetate (50 g, 0.38 mole) and dibutylamine (49.65 g, 0.38 mole) was heated to 150° C. for one day. After cooling, the reaction mixture was taken up in 500 ml of ethyl ether and washed with 200 ml of 1N HCl and 200 ml of water. The ether phase was anhydrified over sodium sulfate, and evaporated to dryness thus yielding 86.7 g of a crude which was distilled under vacuum to give 54.86 g (yield: 67%) of N,N-dibutyl-3-oxo-butanamide.

Workup

  1. temperatureAfter cooling
  2. washwashed with 200 ml of 1N HCl and 200 ml of water
  3. customevaporated to dryness
  4. customthus yielding 86.7 g of a crude which
  5. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-43ba1776ad0d4475bd7f9e0bb00232af
Source dataset
uspto-grants-1998_10
Patent number
US05827881

Reaction notes

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