Ethanol → Butanamide, N,N-diethyl-

HRID 280404Notes

Reaction equation

HRID 280404 reaction equation
[CH2:1]([N:3]([CH2:9][CH3:10])[C:4](=[O:8])/[CH:5]=[CH:6]/[CH3:7])[CH3:2].C(O)C.[H][H]>N1C=CC=CC=1>[CH2:1]([N:3]([CH2:9][CH3:10])[C:4](=[O:8])[CH2:5][CH2:6][CH3:7])[CH3:2].[CH2:1]([N:3]([CH2:9][CH3:10])[C:4](=[O:8])[CH2:5][CH:6]=[CH2:7])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 53544532-ButenaMide, N,N-diethyl-, (E)-2×HCID 178418361HCID 178418361, compound

Product 2

HCID 66192Butanamide, N,N-diethyl-HCID 12545744N,N-Diethylbut-3-enamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

56.5 g of crotonic acid diethylamide 36.9 g of ethanol, 1.27 g of pyridine and 2.74 g of Co2 (CO)8 are reacted analogously to Example 1 for 1.5 hours at 170° C. under a carbon monoxide pressure of 150 bar (+approx. 2% by volume of hydrogen). Analysis showed that 99.6 mol % of the crotonic acid diethylamide had reacted. Relative to this, C5 -dicarboxylic acid derivatives containing mixed derivative groups had been formed at a selectivity of conversion of 97.4 mol %; 2-methylsuccinic acid 1-ethylester-4-diethylamide was 93.6% of this. In addition, butyric acid diethylamide and but-3-enoic acid diethylamide had been formed at selectivities of conversion of 1.2 mol % and 0.4 mol %, respectively.

Workup

  1. customhad reacted
  2. additioncontaining
  3. additionmixed derivative groups
  4. customhad been formed at a selectivity of conversion of 97.4 mol %

Sources & evidence

ORD record
ord-d8a8898b7e9a43319fd2142c67bb9229
Source dataset
uspto-grants-1986_05
Patent number
US04588833

Reaction notes

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