Potassium Iodide → HCID 22130584, compound

HRID 1857751Notes

Reaction equation

HRID 1857751 reaction equation
[I-].[K+].C[Si](Cl)(C)C.[CH2:8]([O:15][CH2:16][C:17]1[N:18]([CH2:34][C:35]2[CH:36]=[CH:37][C:38]([O:41]C)=[N:39][CH:40]=2)[C:19]([S:25][C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=2)=[C:20]([CH:22]([CH3:24])[CH3:23])[N:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(#N)C>[CH2:8]([O:15][CH2:16][C:17]1[N:18]([CH2:34][C:35]2[CH:36]=[CH:37][C:38](=[O:41])[NH:39][CH:40]=2)[C:19]([S:25][C:26]2[CH:27]=[C:28]([Cl:33])[CH:29]=[C:30]([Cl:32])[CH:31]=2)=[C:20]([CH:22]([CH3:24])[CH3:23])[N:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 6397ChlorotrimethylsilaneHCID 22130117HCID 22130117, compound

Product 1

HCID 22130584HCID 22130584, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 83 mg of potassium iodide in acetonitrile was added 64 μl of trimethylsilyl chloride under ice-cooling and stirring. The mixture was allowed to warm up, and after 10 minutes, 150 mg of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-1-(2-methoxypyridin-5-ylmethyl)-4-isopropyl-1H-imidazole was added, and the mixture was stirred with heating at 60° C. After 1 hour, the solution was distilled off under reduced pressure, an aqueous sodium hydrogen carbonate solution was added, extracted with ethyl acetate, the extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate: methanol=10:1) to give 50 mg of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-1-(6-oxo-1,6-dihydro-pyridin-3-yl)methyl-4-isopropyl-1H-imidazole (115a) (yield 34%).

Workup

  1. temperaturecooling
  2. temperatureto warm up
  3. stirringthe mixture was stirred
  4. waitAfter 1 hour
  5. distillationthe solution was distilled off under reduced pressure
  6. additionan aqueous sodium hydrogen carbonate solution was added
  7. extractionextracted with ethyl acetate
  8. dry with materialthe extract was dried over sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel chromatography (ethyl acetate: methanol=10:1)

Sources & evidence

ORD record
ord-679c693607ce4ea48f886321e8e6606b
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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