Acetic Acid → HCID 54574887, compound

HRID 1387336Notes

Reaction equation

HRID 1387336 reaction equation
COC(OC)[N:4]([CH3:6])C.[Cl:9][C:10]1[CH:30]=[CH:29][C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22](=[N:26][O:27][CH3:28])[C:23]([NH2:25])=O)=[CH:12][CH:11]=1.[CH3:31][NH:32]N.C(O)(=O)C>CCOCC>[CH3:28][O:27][N:26]=[C:22]([C:23]1[N:4]([CH3:6])[N:32]=[CH:31][N:25]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][O:14][C:13]1[CH:29]=[CH:30][C:10]([Cl:9])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6061MethylhydrazineHCID 78373Dimethylformamide dimethyl acetalHCID 86584673HCID 86584673, compound

Product 1

HCID 54574887HCID 54574887, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

Dimethylformamide dimethylacetal (0.53 g, 4.5 mmol) was added to 2-(4-chlorophenoxymethyl)-α-methoxyiminophenylacetamide (0.48 g, 1.5 mmol), and the mixture was stirred under reduced pressure (ca. 40 mmHg) at 60° C. for 0.5 hours. After completion of the reaction, the mixture was concentrated under reduced pressure, and a mixture of methylhydrazine (0.08 g, 1.8 mmol) and acetic acid (3 ml) was added to the residue. The mixture was stirred at 90° C. for 1 hour. 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. 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-methyl-1H-1,2,4-triazol-5-yl ketone O-methyloxime (0.31 g, 57.9%) as colorless crystals.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionwas added to the residue
  4. stirringThe mixture was stirred at 90° C. for 1 hour
  5. additionwas added
  6. washthe mixture was washed with saturated aqueous sodium bicarbonate solution (100 ml) twice
  7. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
  10. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-e77bbefc544f42f6ac0f386db0095448
Source dataset
uspto-grants-2001_07
Patent number
US06268312B1

Reaction notes

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