Water → HCID 473919, compound

HRID 1415989Notes

Reaction equation

HRID 1415989 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.O.[NH2:22][NH2:23].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][NH2:23])=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 4739145-(3,5-Dimethylphenylthio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde

Product 1

HCID 473919HCID 473919, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 2 ml of ethanol was dissolved 50 mg (0.17 mmol)of 5-(3,5-dimethylphenylthio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde (Compound I-6), followed by addition of 26 mg (0.5 mmol)of hydrazine hydrate, and the mixture was stirred at room temperature for 15 minutes. 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 n-hexane to precipitate the product, and 34 mg (yield 65%)of Compound I-11 was obtained by the filtration. mp 118-119° 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 n-hexane
  6. customto precipitate the product

Sources & evidence

ORD record
ord-d6ea919fdb794d308656e7254cf32420
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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