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

HRID 1857722Notes

Reaction equation

HRID 1857722 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+]>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

6

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 1

HCID 6344DichloromethaneSolvent

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. temperatureUnder ice-cooling
  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:n-hexane=1:1)

Sources & evidence

ORD record
ord-7d98152e465147fb8d1624739434e69c
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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