2-Furancarboxylic acid → N-[3-(1H-Imidazol-1-yl)propyl]-3-furanecarboxamide

HRID 1154329Notes

Reaction equation

HRID 1154329 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1C(O)=O.[O:9]1CCC[CH2:10]1.Cl.Cl.[N:16]1([CH2:21][CH2:22][CH2:23][NH2:24])[CH:20]=[CH:19][N:18]=[CH:17]1>O>[N:16]1([CH2:21][CH2:22][CH2:23][NH:24][C:10]([C:4]2[CH:3]=[CH:2][O:1][CH:5]=2)=[O:9])[CH:20]=[CH:19][N:18]=[CH:17]1

Participants

5

Reactant 3

HCID 69192-Furancarboxylic acidHCID 8028TetrahydrofuranHCID 122509693-(Imidazole-1-yl)-propylamine Dihydrochloride

Product 1

HCID 13371097N-[3-(1H-Imidazol-1-yl)propyl]-3-furanecarboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.24 g. of furoic acid, 3.24 g. of N,N'-carbonyldiimidazole and 80 ml. of tetrahydrofuran was allowed to stir at room temperature for 2 hours. A 4.0 g. portion of 1H-imidazole-1-propanamine dihydrochloride was added and the mixture was stirred at room temperature overnight. The mixture was then heated for 5 hours, 5 ml. of water was added, heating resumed for 30 minutes and then the mixture was concentrated to remove most of the solvent. Dichloromethane and 60 ml. of 1N sodium hydroxide were added, the organic layer was separated, washed twice with water, dried and concentrated, giving 2.0 g. of the desired product, m.p. 127°-129° C.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. temperatureThe mixture was then heated for 5 hours
  3. temperatureheating
  4. waitresumed for 30 minutes
  5. concentrationthe mixture was concentrated
  6. customto remove most of the solvent
  7. additionof 1N sodium hydroxide were added
  8. customthe organic layer was separated
  9. washwashed twice with water
  10. customdried
  11. concentrationconcentrated
  12. customgiving 2.0 g

Sources & evidence

ORD record
ord-fcf3f8b049474c0e90fe5332362c1007
Source dataset
uspto-grants-1984_12
Patent number
US04489089

Reaction notes

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