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

HRID 1387340Notes

Reaction equation

HRID 1387340 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 acetatein-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 acetatein-hexane

Sources & evidence

ORD record
ord-c45e2e69e88c4673add02f7940792032
Source dataset
uspto-grants-2001_07
Patent number
US06268312B1

Reaction notes

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