Acetyl chloride → 2-((5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methylimidazol-2-yl)methoxy)ethyl acetate

HRID 1416016Notes

Reaction equation

HRID 1416016 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][O:17][CH2:18][CH2:19][OH:20])=[N:12][C:11]=2[CH:21]([CH3:23])[CH3:22])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32].C(=O)([O-])O.[Na+]>CCCCCC.C(Cl)Cl>[C:31]([O:20][CH2:19][CH2:18][O:17][CH2:16][C:13]1[N:14]([CH3:15])[C:10]([S:9][C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)=[C:11]([CH:21]([CH3:23])[CH3:22])[N:12]=1)(=[O:33])[CH3:32]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 54460378HCID 54460378, compound

Product 1

HCID 4739692-((5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methylimidazol-2-yl)methoxy)ethyl acetateYield 95.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To dry methylene chloride solution (5 ml)of 200 mg (0.5 mmol)of 2-{[5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methoxy}ethanol (25a), 161 mg (1.60 mmol)of triethylamine was added under ice-cooling, 63 mg (0.8 mmol)of acetyl chloride was added, and the mixture was stirred at the same temperature for 15 minutes. To the reaction mixture, a saturated aqueous solution of sodium hydrogen carbonate was added, neutralized, and extracted with methylene chloride. The extract was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate:n-hexane=1:1)to obtain 200 mg of 2-[5-(3,5-dichlorophenylthio)-4-isopropyl-1-methylimidazol-2-ylmethoxy]ethyl acetate (Compound I-60)as oil (yield 90%).

Workup

  1. temperaturecooling
  2. extractionextracted with methylene chloride
  3. washThe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel chromatography (ethyl acetate

Sources & evidence

ORD record
ord-6b1e8bba575e4afd8370077aa6190be7
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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