Adipic Acid → n,n-diethylpentanamide

HRID 280405Notes

Reaction equation

HRID 280405 reaction equation
[CH2:1]([N:3]([CH2:10][CH3:11])[C:4](=[O:9])[CH2:5][CH:6]=[CH:7][CH3:8])[CH3:2].C(O)C.C(O)(=O)CCCCC(O)=O>N1C=CC=CC=1>[CH2:10]([N:3]([CH2:1][CH3:2])[C:4](=[O:9])[CH:5]=[CH:6][CH2:7][CH3:8])[CH3:11].[CH2:10]([N:3]([CH2:1][CH3:2])[C:4](=[O:9])[CH2:5][CH2:6][CH2:7][CH3:8])[CH3:11]

Participants

6

Reactant 3

HCID 196Adipic AcidHCID 702EthanolHCID 5677803-Pentenamide, N,N-diethyl-2×

Product 2

HCID 285599n,n-diethylpentanamideHCID 53924574HCID 53924574, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

77.6 g of pent-3-enoic acid diethylamide, 32.2 g of ethanol, 1.58 g of pyridine and 3.42 g of Co2 (CO)8 were reacted, as described in Example 1, for 1 hour at 170° C. under a carbon monoxide pressure of 150 bar (+approx. 2% by volume of H2). After cooling, analysis indicated a conversion of pent-3-enoic acid diethylamide of 47.3 mol %. Relative to this, 61.5 mol % of C6 -dicarboxylic acid ethylester-diethylamides had been formed and these had the following composition: 64.6% (=I1) of 2-ethylsuccinic acid 1-ethylester-4-diethylamide, 29.2% of 2-methylglutaric acid 1-ethylester-5-diethylamide and 6.2% of adipic acid ethylesterdiethylamide. Furthermore, as well as isomers of pentenoic acid diethylamide, n-pentanoic acid diethylamide and C6 -dicarboxylic acid bisdiethylamides (3 isomers) were formed at selectivities of conversion of 1.7 mol % and 1.1 mol %, respectively.

Workup

  1. temperatureAfter cooling
  2. customhad been formed

Sources & evidence

ORD record
ord-02593f30af49449aad3b58787b0a4074
Source dataset
uspto-grants-1986_05
Patent number
US04588833

Reaction notes

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