Benzoic Acid → N-[3-(1H-imidazol-1-yl)propyl]benzamide

HRID 1589176Notes

Reaction equation

HRID 1589176 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.O1CCCC1.Cl.Cl.[N:29]1([CH2:34][CH2:35][CH2:36][NH2:37])[CH:33]=[CH:32][N:31]=[CH:30]1>O>[N:29]1([CH2:34][CH2:35][CH2:36][NH:37][C:1](=[O:9])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:33]=[CH:32][N:31]=[CH:30]1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 122509693-(Imidazole-1-yl)-propylamine Dihydrochloride

Product 1

HCID 3584880N-[3-(1H-imidazol-1-yl)propyl]benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.22 g. of benzoic acid, 1.62 g. of 1,1'-carbonyldiimidazole and 30 ml. of tetrahydrofuran was stirred for 3 hours, then 1.98 g. of 1H-imidazole-1-propanamine dihydrochloride was added. The reaction mixture was stirred for 18 hours, then heated at reflux for 5 hours, then diluted with 5 ml. of water and heated for an additional 30 minutes. The mixture was concentrated to remove most of the solvent and to the residue was added chloroform and 35 ml. of 1N sodium hydroxide. The layers were separated. The organic layer was washed with water, dried over magnesium sulfate, concentrated and diethyl ether was added, giving the desired product, m.p. 134°-136° C.

Workup

  1. additionA mixture of 1.22 g
  2. temperatureheated
  3. temperatureat reflux for 5 hours
  4. additiondiluted with 5 ml
  5. concentrationThe mixture was concentrated
  6. customto remove most of the solvent and to the residue
  7. additionwas added chloroform and 35 ml
  8. customThe layers were separated
  9. washThe organic layer was washed with water
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated
  12. additiondiethyl ether was added

Sources & evidence

ORD record
ord-2e1c3b8836f5483abd58430c707b46a2
Source dataset
uspto-grants-1986_02
Patent number
US04568687

Reaction notes

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