Acetic Acid → 1-[2-(4-Acetylcarbamoylphenoxy)ethyl]imidazole

HRID 745924Notes

Reaction equation

HRID 745924 reaction equation
[C:1](O)(=[O:3])[CH3:2].[C:5]([C:8]1[CH:21]=[CH:20][C:11]([O:12][CH2:13][CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[CH:10][CH:9]=1)(=[O:7])[NH2:6]>CN(C)C=O>[C:1]([NH:6][C:5]([C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[CH:20][CH:21]=1)=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 135691774-(2-(1H-imidazol-1-yl)ethoxy)benzamide

Product 1

HCID 135692001-[2-(4-Acetylcarbamoylphenoxy)ethyl]imidazoleYield 16.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N'-Carbonyldiimidazole (4.9 g) was dissolved in dry N,N-dimethylformamide (10 ml) and acetic acid (1.8 g) was added. The solution was stirred for 5 minutes and then 1-[2-(4-carbamoylphenoxy)ethyl]imidazole (4.6 g) was added. The solution was heated under reflux for 3 hours and then evaporated. The residue was treated with aqueous sodium bicarbonate and the mixture was extracted several times with ethyl acetate. The combined ethyl acetate extracts were washed with water, dried (Na2SO4) and evaporated to give an oil which was chromatographed on silica gel. Elution with chloroform gave some impurity. Further elution with chloroform/methanol (50:1) gave a solid which was crystallised from 2-butanone to give 1-[2-(4-acetylcarbamoylphenoxy)ethyl]imidazole (0.9 g), m.p. 164°-165° C. Found: C, 61.28; H, 5.54; N, 15.51. C14H15N3O3 requires: C, 61.53; H, 5.53; N, 15.38%.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 3 hours
  3. customevaporated
  4. additionThe residue was treated with aqueous sodium bicarbonate
  5. extractionthe mixture was extracted several times with ethyl acetate
  6. washThe combined ethyl acetate extracts were washed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customto give an oil which
  10. customwas chromatographed on silica gel
  11. washElution with chloroform
  12. customgave some impurity
  13. washFurther elution with chloroform/methanol (50:1)
  14. customgave a solid which
  15. customwas crystallised from 2-butanone

Sources & evidence

ORD record
ord-5702eba68a6b49f68596ba3d99a74eb5
Source dataset
uspto-grants-1986_07
Patent number
US04602016

Reaction notes

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