Dimethyl Sulfate → HCID 22130857, compound

HRID 1857771Notes

Reaction equation

HRID 1857771 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[NH:13][C:14]([S:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](=O)([O-])[O-].[Li+].[Li+].S(OC)(OC)(=O)=O>C(#N)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]([CH3:29])[C:14]([S:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11125Lithium CarbonateHCID 178440070HCID 178440070, compound

Product 1

HCID 22130857HCID 22130857, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

In 25 ml of dry acetonitrile was dissolved 5.0 g (11.5 mmol) of imidazole (101e), followed by addition of 1.7 g (23 ml) of lithium carbonate and 2.2 g (17.4 mmol) of dimethyl sulfate. The mixture was stirred under heating at 70° C. for 2 hours. The reactLion mixture was diluted with 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 column chromatography (ethyl acetate) to provide 3.1 g (yield 60%) of 2-(3-benzyloxypropyl)-5-(3,5-dichlorophenyl-thio)-4-isopropyl-1-methyl-1H-imidazole (136a) as oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-09c497247743480b8d0246e473744b2e
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

Loading…