Potassium Iodide → 1-acetylmethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole

HRID 1857707Notes

Reaction equation

HRID 1857707 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].[I-].[K+].[Cl:8][C:9]1[CH:10]=[C:11]([S:16][C:17]2[NH:21][C:20]([CH2:22][O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[N:19][C:18]=2[CH:33]([CH3:35])[CH3:34])[CH:12]=[C:13]([Cl:15])[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:3]([CH2:2][N:21]1[C:17]([S:16][C:11]2[CH:12]=[C:13]([Cl:15])[CH:14]=[C:9]([Cl:8])[CH:10]=2)=[C:18]([CH:33]([CH3:34])[CH3:35])[N:19]=[C:20]1[CH2:22][O:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1)(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 178491401HCID 178491401, compound

Product 1

HCID 221309871-acetylmethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazoleYield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In acetone (2 ml) was dissolved 111 mg (1.20 mmol) of chloroacetone, followed by addition of 200 mg (1.2 mmol) of potassium iodide, and the mixture was stirred at room temperature for 15 minutes. Then, 437 mg (1.00 mmol) of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole (16b) and 170 mg (1.20 mmol) of potassium carbonate were added in order, and the mixture was stirred for 5 hours and was left overnight. This reaction mixture was concentrated under reduced pressure and the residue was extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous sodium sulfate and the solvent was concentrated under reduced pressure. The residue was fractionated by silica gel chromatography (ethyl acetate:methylene chloride=1:9). The oil was crystallized from ether to provide 270 mg (yield 62%) of 1-acetylmethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole (17v). mp 87-90° C.

Workup

  1. stirringthe mixture was stirred for 5 hours
  2. waitwas left overnight
  3. concentrationThis reaction mixture was concentrated under reduced pressure
  4. extractionthe residue was extracted with methylene chloride
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customThe oil was crystallized from ether

Sources & evidence

ORD record
ord-489ff2ed9fa84781a7261c9158ef44b2
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

Loading…