Hydrochloric Acid → 2-[2-(2,5-Dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamide

HRID 1779725Notes

Reaction equation

HRID 1779725 reaction equation
[OH-:1].[K+].C1(C)C=CC=CC=1.[CH3:10][C:11]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:12]=1[O:13][CH2:14][C:15]1[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=1[C:17]([C:21]#[N:22])=[N:18][O:19][CH3:20].Cl>O>[CH3:10][C:11]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:12]=1[O:13][CH2:14][C:15]1[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=1[C:17](=[N:18][O:19][CH3:20])[C:21]([NH2:22])=[O:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 14797Potassium HydroxideHCID 54390956HCID 54390956, compound

Product 1

HCID 542571262-[2-(2,5-Dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamideYield 83.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

85% Potassium hydroxide (0.40 g, 6.0 mmol) and toluene (5 ml) were added to 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminobenzyl cyanide (E/Z=15/85)(1.47 g, 5.0 mmol). The mixture was stirred at 95° C. for 2 hours. After completion of the reaction, water was added. The mixture was neutralized with conc. hydrochloric acid, extracted with toluene (100 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamide (1.30 g, Yield: 83.2%, E/Z=15/85).

Workup

  1. additionwas added
  2. extractionextracted with toluene (100 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-93059a2bea6a49d0af2c483766fedcd7
Source dataset
uspto-grants-1997_05
Patent number
US05627284

Reaction notes

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