Ethanol → 2-(1-Benzyl-5-methyl-4-imidazolyl)-4-oxotetrahydrothiophene oxime

HRID 27183Notes

Reaction equation

HRID 27183 reaction equation
[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH:14]2[CH2:18][C:17](=O)[CH2:16][S:15]2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.Cl.[OH:24][NH2:25].C([O-])(=O)C.[Na+]>O>[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH:14]2[CH2:18][C:17](=[N:25][OH:24])[CH2:16][S:15]2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 233436792-(1-Benzyl-5-methyl-4-imidazolyl)-4-oxotetrahydrothiophene

Product 1

HCID 867371812-(1-Benzyl-5-methyl-4-imidazolyl)-4-oxotetrahydrothiophene oxime

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(1-Benzyl-5-methyl-4-imidazolyl)-4-oxotetrahydrothiophene (0.14 g., 0.5 mole) is dissolved in 1 ml. of ethanol and 1 ml. of water is added. Then hydroxyamine hydrochloride (38 mg., 0.55 mole) and sodium acetate (45 mg., 0.55 mole) are added. The mixture is stirred at room temperature overnight. The reaction mixture is concentrated in vacuo. The residue is triturated with chloroform and the mixture is filtered. The chloroform extract is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude oxime, 2-(1-benzyl-5-methyl-4-imidazolyl)-4-oxotetrahydrothiophene oxime, is a brown viscous oil (0.15 g.).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customThe residue is triturated with chloroform
  3. filtrationthe mixture is filtered
  4. extractionThe chloroform extract
  5. dry with materialis dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31bea89f94fe486db9b7de125628220f
Source dataset
uspto-grants-1980_09
Patent number
US04220654

Reaction notes

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