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

HRID 1416030Notes

Reaction equation

HRID 1416030 reaction equation
Cl.[CH3:2][N:3]1[C:7]([S:8][C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[CH:10]=2)=[C:6]([CH:17]([CH3:20])[C:18]#N)[N:5]=[C:4]1[CH3:21].C[OH:23].[C:24](=O)([O-])[OH:25].[Na+]>CO.C(OCC)C.O>[CH3:2][N:3]1[C:7]([S:8][C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[CH:10]=2)=[C:6]([CH:17]([CH3:20])[C:18]([O:25][CH3:24])=[O:23])[N:5]=[C:4]1[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 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 962WaterSolventHCID 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)to

Sources & evidence

ORD record
ord-be19657f7bef42eb8c26bd6fe2f28293
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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