Imidazole → HCID 67780593, compound

HRID 1757440Notes

Reaction equation

HRID 1757440 reaction equation
[Cl:1][CH2:2][CH2:3][C:4](=[O:11])[CH2:5][C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[ClH:1].[N:12]1([CH2:2][CH2:3][C:4](=[O:11])[CH2:5][C:6]2[S:7][CH:8]=[CH:9][CH:10]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 19388019HCID 19388019, compound

Product 1

HCID 67780593HCID 67780593, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

18.9 g (0.10 mol) of 4-chloro-1-(2-thienyl)butanone are run into a solution, maintained at about 90° C., of 15 g (0.22 mol) of imidazole in 35 ml of toluene, and the mixture is heated to reflux for 4 hours. The reaction medium is diluted with ethyl acetate and the mixture is washed with water and extracted with dilute hydrochloric acid solution.The aqueous phase is alkalinised with sodium hydroxide and extracted with ethyl acetate, which is dried over dry sodium sulphate. The solution is treated with a solution of hydrogen chloride in ethanol, and the insolublematter purified by a wash in acetone, to give 6 g of a water-soluble, beigepowder.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 4 hours
  3. washthe mixture is washed with water
  4. extractionextracted with dilute hydrochloric acid solution.The aqueous phase
  5. extractionextracted with ethyl acetate, which
  6. dry with materialis dried over dry sodium sulphate
  7. additionThe solution is treated with a solution of hydrogen chloride in ethanol
  8. customthe insolublematter purified by
  9. washa wash in acetone
  10. customto give 6 g of a water-soluble, beigepowder

Sources & evidence

ORD record
ord-5e0dfa3ae589444b9f747a1ce7a2b35e
Source dataset
uspto-grants-1995_08
Patent number
US05446060

Reaction notes

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