Hydrochloric Acid → HCID 178475916, compound

HRID 1857725Notes

Reaction equation

HRID 1857725 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[NH:14][C:13]([CH3:15])=[N:12][C:11]=2[CH2:16][OH:17])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(N(CC)CC)C.[C:25](Cl)(=[O:27])[CH3:26].Cl.C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:25]([O:17][CH2:16][C:11]1[N:12]=[C:13]([CH3:15])[NH:14][C:10]=1[S:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=1)(=[O:27])[CH3:26]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178425336HCID 178425336, compound

Product 1

HCID 178475916HCID 178475916, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dry methylene chloride (85 ml) was dissolved 1.7 g (6.8 mmol) of [5-(3,5-dimethylphenylthio)-2-methyl-1H-imidazol-4-yl]methanol (41d), followed by addition of 2.10 g (20.8 mmol) of triethylamine. To this solution, acetyl chloride was added dropwise with stirring under ice-cooling. At the same temperature, the mixture was stirred for 30 minutes, then, 8.3 ml of 6N hydrochloric acid was added, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution to neutralize, 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) to obtain 1.55 g of [5-(3,5-dimethylphenylthio)-2-methyl-1H-imidazol-4-yl]methyl acetate (41b) as oil (yield 78%).

Workup

  1. temperaturecooling
  2. stirringAt the same temperature, the mixture was stirred for 30 minutes
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. extractionextracted with methylene chloride
  5. washThe extract was washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-6c6987b958c14610acec8b2ddd59a886
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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