Potassium Iodide → HCID 22130068, compound

HRID 1857783Notes

Reaction equation

HRID 1857783 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:28][C:29](=[O:31])[CH3:30].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:8][CH2:9][C:10]1[N:11]([CH2:28][C:29](=[O:31])[CH3:30])[C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 1784190342-Benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole

Product 1

HCID 22130068HCID 22130068, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 20 ml of acetone was dissolved 5.0 g of the imidazole (101a) and 1.36 g (14.7 mmol) of monochloroacetone, followed by addition of 2.46 g (12.27 mmol) of potassium iodide, and the mixture was stirred at room temperature for 30 minutes. Then, to the mixture was added 2.04 g (14.8 mmol) of potassium carbonate, and the mixture was stirred with heating at 50° C. for 4 hours and worked up. The reaction mixture was distilled off under reduced pressure, and the residue was extracted with methylene chloride. The extract was washed with water, dried and the solvent was distilled off. The residue was purified by silica gel column chromatography (methylene chloride:ethyl acetate=9:1) to provide 3.1 g (yield 54%) of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-acetylmethyl-1H-imidazole (139) as solid.

Workup

  1. stirringthe mixture was stirred
  2. temperaturewith heating at 50° C. for 4 hours
  3. distillationThe reaction mixture was distilled off under reduced pressure
  4. extractionthe residue was extracted with methylene chloride
  5. washThe extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by silica gel column chromatography (methylene chloride:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-8e772ed2720a431bbcbe2699f7f1f3c4
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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