Ethylenediamine → N-(2-aminoethyl)thiophene-2-carboxamide

HRID 1589199Notes

Reaction equation

HRID 1589199 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8]CC)=O.[CH2:11]([NH2:14])[CH2:12][NH2:13]>C1(C)C=CC=CC=1>[NH2:13][CH2:12][CH2:11][NH:14][C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 76052Ethyl 2-thenoate

Product 1

HCID 4649097N-(2-aminoethyl)thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
97.5 °C

Procedure

A mixture of ethyl thiophene-2-carboxylate (12.0 g.) and ethylenediamine (15.4 ml.) was heated at 95-100° C. for 48 hours. Excess ethylenediamine was removed under reduced pressure and the residue was dissolved in water (150 ml.). The insoluble material [bis(carboxamide)derivative] was removed by filtration. Evaporation of the filtrate gave a residue which was dissolved in toluene (50 ml.). The mixture was evaporated to give N-(2-aminoethyl)-thiophene-2-carboxamide as an oil (12.0 g.) essentially pure by TLC (Rf 0.90; Si02 : 10% v/v methanol in chloroform as eluant) which was used without purification.

Workup

  1. customExcess ethylenediamine was removed under reduced pressure
  2. dissolutionthe residue was dissolved in water (150 ml.)
  3. customThe insoluble material [bis(carboxamide)derivative] was removed by filtration
  4. customEvaporation of the filtrate
  5. customgave a residue which
  6. customThe mixture was evaporated

Sources & evidence

ORD record
ord-75d163724c0846ce93ba2bd13c47c536
Source dataset
uspto-grants-1986_02
Patent number
US04568691

Reaction notes

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