Methanol → Methyl 2-{5-[(3,5-dimethylphenyl)sulfanyl]-1,2-dimethyl-1H-imidazol-4-yl}propanoate

HRID 1857729Notes

Reaction equation

HRID 1857729 reaction equation
[CH3:1][N:2]1[C:6]([S:7][C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=2)=[C:5]([CH:16]([CH3:19])[C:17]#N)[N:4]=[C:3]1[CH3:20].C[OH:22].O.[C:24](=O)([O-])[OH:25].[Na+]>CO.C(OCC)C.Cl>[CH3:1][N:2]1[C:6]([S:7][C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=2)=[C:5]([CH:16]([CH3:19])[C:17]([O:25][CH3:24])=[O:22])[N:4]=[C:3]1[CH3:20]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 516892Sodium BicarbonateHCID 22130065HCID 22130065, compound

Product 1

HCID 474005Methyl 2-{5-[(3,5-dimethylphenyl)sulfanyl]-1,2-dimethyl-1H-imidazol-4-yl}propanoate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21864698Diethyl ether methanolSolvent

Procedure

In 5 ml of methanol/diethyl ether (1/3 v/v %) saturated with hydrogen chloride was dissolved 60 mg (0.21 mmol) of 2-[1,2-dimethyl-5-(3,5-dimethylphenylthio)-1H-imidazol-4-yl]propiononitrile (43a), and the mixture was left at 4° C. for 23 hours. To the reaction mixture, 2 ml of methanol and 0.3 ml of water were added, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was added to a saturated aqueous sodium hydrogen carbonate solution and 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) to obtain 57 mg of Compound I-96 as oil (yield 85%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-41c0c185e24e426b9ae2968aef9fc655
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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