Acetic Acid → HCID 53806169, compound

HRID 1387337Notes

Reaction equation

HRID 1387337 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-a5e02afcb3ac44f7a15091691854cfc7
Source dataset
uspto-grants-2001_07
Patent number
US06268312B1

Reaction notes

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