Acetic Acid → HCID 53806169, compound

HRID 279452Notes

Reaction equation

HRID 279452 reaction equation
O1CCOCC1.C(O)(=O)C.[Cl:11][C:12]1[CH:35]=[CH:34][C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24](=[N:31][O:32][CH3:33])[C:25]([N:27]=[CH:28][NH:29][OH:30])=O)=[CH:14][CH:13]=1>CCOCC>[CH3:33][O:32][N:31]=[C:24]([C:25]1[O:30][N:29]=[CH:28][N:27]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][O:16][C:15]1[CH:34]=[CH:35][C:12]([Cl:11])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 312751,4-DioxaneHCID 178502837HCID 178502837, compound

Product 1

HCID 53806169HCID 53806169, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

Dioxane (2 ml) and acetic acid (1.5 ml) were added to 2-(4-chlorophenoxymethyl)-N-hydroxyaminomethylene-α-methoxyiminophenylacetamide (0.36 g, 1 mmol), and the mixture was stirred at 120° C. for 4 hours. After completion of the reaction, ether (150 ml) was added, and the mixture was washed with saturated aqueous sodium bicarbonate solution (100 ml) twice. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give 2-(4-chlorophenoxymethyl)phenyl 1,2,4-oxadiazol-5-yl ketone O-methyloxime (0.14 g, 40.8%) as colorless crystals.

Workup

  1. additionwas added
  2. washthe mixture was washed with saturated aqueous sodium bicarbonate solution (100 ml) twice
  3. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
  6. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-6ac3e62214dc4b21a12909448a62deb7
Source dataset
uspto-grants-2002_03
Patent number
US06362212B1

Reaction notes

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