Ethylorthoformate → 2-(2,5-dimethylphenoxymethyl)phenyl 1,3,4-oxadiazol-2-yl ketone O-methyloxime

HRID 279455Notes

Reaction equation

HRID 279455 reaction equation
[CH:1]([O-])([O-])OCC.[CH3:7][C:8]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[N:23][O:24][CH3:25])[C:19]([NH:21][NH2:22])=[O:20]>O>[CH3:25][O:24][N:23]=[C:18]([C:19]1[O:20][CH:1]=[N:22][N:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][O:10][C:9]1[CH:26]=[C:27]([CH3:30])[CH:28]=[CH:29][C:8]=1[CH3:7]

Participants

4

Reactant 2

HCID 53630039EthylorthoformateHCID 865846752-(2,5-Dimethylphenoxymethyl)-alpha-methoxyiminophenylacetohydrazide

Product 1

HCID 542136592-(2,5-dimethylphenoxymethyl)phenyl 1,3,4-oxadiazol-2-yl ketone O-methyloximeYield 19.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl orthoformate (2 ml) was added to 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetohydrazide (0.49 g, 1.5 mmol), and the mixture was stirred under reflux for 4 hours. After completion of the reaction, water (100 ml) was added, and the mixture was extracted with dichloromethane. The dichloromethane layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give 2-(2,5-dimethylphenoxymethyl)phenyl 1,3,4-oxadiazol-2-yl ketone O-methyloxime (0.10 g, 19.8%) as colorless crystals.

Workup

  1. temperatureunder reflux for 4 hours
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-1fb2cea9cd2042dd96ce484c6e97769f
Source dataset
uspto-grants-2002_03
Patent number
US06362212B1

Reaction notes

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