Hydrochloric Acid → (2E)-2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxyiminoacetamide

HRID 1756732Notes

Reaction equation

C1(C)C=CC=CC=1.Cl.[CH3:9][C:10]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[N:24][O:25][CH3:26])[C:21]([NH2:23])=[O:22]>O>[CH3:9][C:10]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1/[C:20](=[N:24]\[O:25][CH3:26])/[C:21]([NH2:23])=[O:22]

Participants

Conditions

Temperature: 85 °C

Procedure

Toluene (4 ml) and conc. hydrochloric acid (0.8 ml) were added to 2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamide (E/Z=15/85) (1.25 g, 4.0 mmol), and the mixture was stirred at 85° C. for 2 hours. After the reaction, water (80 ml) was added. The mixture was extracted with toluene (80 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give crystals. The crystals were recrystallized from n-hexane/ethyl acetate to give (E)-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamide (1.02 g, Yield: 81.6%) as colorless crystals.

Workup

additionwas added
extractionThe mixture was extracted with toluene (80 ml)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customto give crystals
customThe crystals were recrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record: ord-ae92db095bc44cc3bc5474b1fd02c518
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05442063

Reaction notes

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