Potassium Carbonate → 1-[4-(4-Chlorophenyl)-2-(4-acetylaminophenylthio)-n-butyl]imidazole

HRID 463283Notes

Reaction equation

HRID 463283 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11](OS(C)(=O)=O)[CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:5][CH:4]=1.[C:23]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([SH:33])=[CH:29][CH:28]=1)(=[O:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CO>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH:11]([S:33][C:30]2[CH:29]=[CH:28][C:27]([NH:26][C:23](=[O:25])[CH3:24])=[CH:32][CH:31]=2)[CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 707774'-MercaptoacetanilideHCID 202825741-[4-(4-Chlorophenyl)-2-(methanesulfonyloxy)-n-butyl]imidazole hydrochloride

Product 1

HCID 134573281-[4-(4-Chlorophenyl)-2-(4-acetylaminophenylthio)-n-butyl]imidazoleYield 84%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

A mixture of 1-[4-(4-chlorophenyl)-2-methanesulfonyloxy-n-butyl]imidazole hydrochloride (2.0 g), 4-acetylaminothiophenol (1.2 g) and anhydrous potassium carbonate (2.0 g) in 30 ml of acetone and 10 ml of methanol was stirred and refluxed overnight under nitrogen. The solvent was evaporated and the residue treated with water (50 ml) and ether (20 ml) and the mixture stirred until crystallization was complete. Filtration of the product and recrystallization from ethyl acetate gave 1.84 g of 1-[4-(4-chlorophenyl)-2-(4-acetylaminophenylthio)-n-butyl]imidazole as a pale cream solid, m.p. 165.5°-166.5° C. B. Similarly, proceeding as above substituting the appropriate thiophenol for 4-acetylaminothiophenol the following compounds are prepared:

Workup

  1. temperaturerefluxed overnight under nitrogen
  2. customThe solvent was evaporated
  3. additionthe residue treated with water (50 ml) and ether (20 ml)
  4. stirringthe mixture stirred until crystallization
  5. filtrationFiltration of the product and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-4362c53482164d248c2e5f727147c609
Source dataset
uspto-grants-1985_05
Patent number
US04518607

Reaction notes

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