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

HRID 463519

Reaction equation

HRID 463519 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

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; SiO2 : 10% v/v methanol in chloroform as eluant) which was used without purification.

Workup

  1. temperaturewas heated at 95°-100° C. for 48 hours
  2. customExcess ethylenediamine was removed under reduced pressure
  3. dissolutionthe residue was dissolved in water (150 ml.)
  4. customThe insoluble material [bis(carboxamide)derivative] was removed by filtration
  5. customEvaporation of the filtrate
  6. customgave a residue which
  7. customThe mixture was evaporated

Sources & evidence

ORD record
ord-bb725bcb229f4b24a4de4c9fd9359245
Source dataset
uspto-grants-1985_05
Patent number
US04520027

Linked notes

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