Methyl iodide → HCID 22130223, compound

HRID 1857713Notes

Reaction equation

HRID 1857713 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[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.[C:26](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH2:1]([O:8][CH2:9][C:10]1[N:14]([CH3:26])[C:13]([CH:15]([CH3:17])[CH3:16])=[C:12]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[N:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178440141HCID 178440141, compound

Product 1

HCID 22130223HCID 22130223, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 218 g of dry dimethylformamide was dissolved 21.8 g (58.5 mmol) of 2-benzyloxymethyl-5-(3-chlorophenylthio)-4-isopropyl-1H-imidazole (16e), followed by addition of 12.2 g (88.3 mmol) of anhydrous potassium carbonate and 11.6 g (81.7 mmol) of methyl iodide, the mixture was stirred at room temperature for 7 hours. To the reaction mixture was added ice-water, and the mixture was extracted with diethyl ether. The extract was washed with water and dried over sodium sulfate. The solvent was concentrated under reduced pressure and the residue was purified by silica gel chromatography (ethyl acetate:methylene chloride=1:8). From the first eluted fraction, 620 mg (yield 3%) of 2-benzyloxymethyl-4-(3-chlorophenylthio)-5-isopropyl-1-methyl-1H-imidazole (17ab') was obtained as oil. From the latter eluted fraction, 17.6 g (yield 78%) of 2-benzyloxymethyl-5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole (17ab) was obtained as oil.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe extract was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (ethyl acetate:methylene chloride=1:8)

Sources & evidence

ORD record
ord-2f1629238fa840f3ab0905cb543a3802
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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