Hydrochloric Acid → HCID 54509160, compound

HRID 1857720Notes

Reaction equation

HRID 1857720 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([S:10][C:11]2[N:15]([CH3:16])[C:14]([CH2:17][O:18][CH:19]3OCCO3)=[N:13][C:12]=2[CH:24]([CH3:26])[CH3:25])[CH:6]=[C:7]([Cl:9])[CH:8]=1.[C:27](=O)([O-])[OH:28].[Na+]>CO>[Cl:9][C:7]1[CH:6]=[C:5]([S:10][C:11]2[N:15]([CH3:16])[C:14]([CH2:17][O:18][CH2:19][CH:27]=[O:28])=[N:13][C:12]=2[CH:24]([CH3:25])[CH3:26])[CH:4]=[C:3]([Cl:2])[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22130107HCID 22130107, compound

Product 1

HCID 54509160HCID 54509160, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a mixture of methanol (1 ml) and 6N-hydrochloric acid (1 ml) was dissolved 156 mg (0.37 mmol) of 5-(3,5-dichlorophenylthio)-2-(1,3-dioxolan-2-yloxymethyl)-4-isopropyl-1-methylimidazole (23a), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution to neutralize, and extracted with methylene chloride. The organic layer was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was fractionated by silica gel chromatography (ethyl acetate) to obtain 39 mg of {[5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methoxy} acetaldehyde (24a) as oil (yield 28%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-492a7f8454ab424da317c4721592162b
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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