Hydrochloric Acid → 2-(2-Phenoxyphenyl)-2-methoxyiminoacetamide

HRID 1779731Notes

Reaction equation

HRID 1779731 reaction equation
[OH-:1].[K+].C1(C)C=CC=CC=1.[O:10]([C:17]1[CH:28]=[CH:27][CH:26]=[CH:25][C:18]=1[C:19]([C:23]#[N:24])=[N:20][O:21][CH3:22])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>O>[O:10]([C:17]1[CH:28]=[CH:27][CH:26]=[CH:25][C:18]=1[C:19](=[N:20][O:21][CH3:22])[C:23]([NH2:24])=[O:1])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 14797Potassium HydroxideHCID 541653652-Phenoxy-alpha-methoxyiminobenzyl cyanide

Product 1

HCID 539671372-(2-Phenoxyphenyl)-2-methoxyiminoacetamideYield 90,275.703%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

85% Potassium hydroxide (1.19 g, 0.018 mol) and toluene (30 ml) were added to 2-phenoxy-α-methoxyiminobenzyl cyanide (E/Z=7/93)(3.78 g, 0.015 mmol). The mixture was stirred at 80° C. for 2.5 hours. After completion of the reaction, water (100 ml) was added. The mixture was neutralized with conc. hydrochloric acid, extracted with ether (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-phenoxyphenyl)-2-methoxyiminoacetamide (3.66 g, Yield: 90.3%, E/Z=6/94).

Workup

  1. additionwas added
  2. extractionextracted with ether (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-e7e6f53ec37a4b1eadcfd9246906561b
Source dataset
uspto-grants-1997_05
Patent number
US05627284

Reaction notes

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