Water → HCID 473918, compound

HRID 1415988Notes

Reaction equation

HRID 1415988 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH:16]=O)=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+].O>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH:16]=[N:22][OH:23])=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 4739145-(3,5-Dimethylphenylthio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehydeHCID 517045Sodium Acetate

Product 1

HCID 473918HCID 473918, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 2 ml of ethanol was dissolved 50 g (0.17 mmol)of 5-(3,5-dimethylphenylthio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde (Compound I-6), followed by addition of 36 mg (0.5 mmol)of hydroxylamine hydrochloride and 43 mg (0.5 mmol) of sodium acetate, and the mixture was stirred for 30 minutes at room temperature. To this reaction mixture, water was added, and the mixture was extracted with methylene chloride. The organic layer was washed with water, dried over sodium sulfate, and the solvent was concentrated under reduced pressure. The residue was washed with ethyl acetate to precipitate the product, and 32 mg (yield 60%)of Compound I-10 was obtained by the filtration. mp 240-241° C.

Workup

  1. extractionthe mixture was extracted 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. washThe residue was washed with ethyl acetate
  6. customto precipitate the product

Sources & evidence

ORD record
ord-fa3db8ad89d140e0acc1043b4786e650
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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