Methyl iodide → 5-(3,5-Dichlorophenylthio)-4-isopropyl-1,2-dimethyl-1H-imidazole

HRID 1857686Notes

Reaction equation

HRID 1857686 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[NH:14][C:13]([CH3:15])=[N:12][C:11]=2[CH:16]([CH3:18])[CH3:17])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].[Na+].[CH3:21]I>CN(C)C=O>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH3:21])[C:13]([CH3:15])=[N:12][C:11]=2[CH:16]([CH3:18])[CH3:17])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178432748HCID 178432748, compound

Product 1

HCID 4739095-(3,5-Dichlorophenylthio)-4-isopropyl-1,2-dimethyl-1H-imidazoleYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dry N,N-dimethylformamide (8 ml) was dissolved 400 mg (1.3 mmol) of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1H-imidazole (5a), followed by addition of 80 mg (2.0 mmol) of sodium hydride under ice-cooling. After 5 minutes, 245 mg (1.73 mmol) of methyl iodide was added. After 30 minutes, the reaction mixture was poured in ice-water and extracted with diethyl ether. The extract was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:n-hexane=1:2) and recrystallized from n-hexane to provide 313 mg (yield 75%) of 5-(3,5-dichlorophenylthio)-1,2-dimethyl-4-isopropyl-1H-imidazole (Compound I-1). mp 95 to 96° C.

Workup

  1. temperaturecooling
  2. waitAfter 30 minutes
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (ethyl acetate:n-hexane=1:2)
  9. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-3595dd2043b340ecb924b48bf18b6870
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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