Tetrahydrofuran → N-[3-(1H-imidazol-1-yl)propyl]-2-phenoxyacetamide

HRID 1589181Notes

Reaction equation

HRID 1589181 reaction equation
[O:1]([CH2:8][C:9]([OH:11])=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:31]1([CH2:36][CH2:37][CH2:38][NH2:39])[CH:35]=[CH:34][N:33]=[CH:32]1>O>[N:31]1([CH2:36][CH2:37][CH2:38][NH:39][C:9](=[O:11])[CH2:8][O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:35]=[CH:34][N:33]=[CH:32]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 19188Phenoxyacetic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 122509693-(Imidazole-1-yl)-propylamine Dihydrochloride

Product 1

HCID 5081968N-[3-(1H-imidazol-1-yl)propyl]-2-phenoxyacetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.28 g. of phenoxyacetic acid, 2.43 g. of 1,1'-carbonyldiimidazole and 50 ml. of tetrahydrofuran was stirred at room temperature for 2 hours, then 3.0 g. of 1H-imidazole-1-propanamine dihydrochloride was added. The reaction mixture was stirred for 18 hours, then heated at reflux temperature for 5 hours, 5 ml. of water was added, the mixture was heated for 30 minutes and then concentrated to remove the tetrahydrofuran. The residue was treated with methylene chloride and 50 ml. of 1N sodium hydroxide and the layers separated. The organic layer was washed with water, dried over magnesium sulfate and concentrated. The residue was washed onto a filter with ether, giving the desired product, m.p. 91°-93° C.

Workup

  1. additionA mixture of 2.28 g
  2. temperatureheated
  3. temperatureat reflux temperature for 5 hours
  4. temperaturethe mixture was heated for 30 minutes
  5. concentrationconcentrated
  6. customto remove the tetrahydrofuran
  7. additionThe residue was treated with methylene chloride and 50 ml
  8. customof 1N sodium hydroxide and the layers separated
  9. washThe organic layer was washed with water
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated
  12. washThe residue was washed onto
  13. filtrationa filter with ether

Sources & evidence

ORD record
ord-de6934bdb7514aa2bab718b2e63cf2d8
Source dataset
uspto-grants-1986_02
Patent number
US04568687

Reaction notes

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