Acetyl chloride → (5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)methanol acetate

HRID 1857717Notes

Reaction equation

HRID 1857717 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][OH:17])=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29].C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:28]([O:17][CH2:16][C:13]1[N:14]([CH3:15])[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:11]([CH:18]([CH3:20])[CH3:19])[N:12]=1)(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 473916(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)methanolHCID 516892Sodium Bicarbonate

Product 1

HCID 473949(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)methanol acetateYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dry methylene chloride (10 ml) was dissolved 220 mg (0.700 mmol) of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methanol (Compound I-8), followed by addition of 201 mg (2.00 mmol) of triethylamine. Then, 78.0 mg (1.00 mmol) of acetyl chloride was added under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. A saturated aqueous sodium hydrogen carbonate solution was added for neutralization, and the mixture was extracted with methylene chloride. The organic layer 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:n-hexane=1:1) to give 170 mg of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methyl acetate (Compound I-40) (yield 69%). mp 92-93° C.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-3fb3b9deb8934d0f843eb2f0eff42dde
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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