Hydrochloric Acid → HCID 85447596, compound

HRID 1779724Notes

Reaction equation

HRID 1779724 reaction equation
[OH-].[K+].C([OH:7])(C)(C)C.[CH3:8][C:9]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:10]=1[O:11][CH2:12][C:13]1[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=1[C:15]([C:18]#[N:19])=[N:16][OH:17].Cl>O>[CH3:8][C:9]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:10]=1[O:11][CH2:12][C:13]1[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=1[C:15](=[N:16][OH:17])[C:18]([NH2:19])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 85405589HCID 85405589, compound

Product 1

HCID 85447596HCID 85447596, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

85% Potassium hydroxide (6.12 g, 92.8 mmol) and tert-butyl alcohol (15 ml) were added to 2-(2,5-dimethylphenoxymethyl)-α-hydroxyiminobenzyl cyanide(E/Z=15/85)(1.30 g, 4.64 mmol). The mixture was heated under reflux for 5 hours. After completion of the reaction, the reaction mixture was neutralized with 6N hydrochloric acid, and water (100 ml) was added. The resulting mixture was extracted with ether (100 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crystals were recrystallized from n-hexane/ethyl acetate to give 2-[2-(2,5dimethylphenoxymethyl)phenyl]-2-hydroxyiminoacetamide (0.83 g, Yield: 60.0%, Z=at least 98%) as colorless crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customAfter completion of the reaction
  4. additionwas added
  5. extractionThe resulting mixture was extracted with ether (100 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting crystals were recrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-6f16bbcb65a24ab49aba28aca0a58bcd
Source dataset
uspto-grants-1997_05
Patent number
US05627284

Reaction notes

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