Hydrochloric Acid → N-(3,5-dimethylphenyl)-2-(hydroxyimino)acetamide

HRID 3107

Reaction equation

HRID 3107 reaction equation
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH3:15][C:16]1[CH:17]=[C:18]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[NH2:19].Cl.Cl.[NH2:26][OH:27]>O>[CH3:15][C:16]1[CH:17]=[C:18]([NH:19][C:3](=[O:5])[CH:2]=[N:26][OH:27])[CH:20]=[C:21]([CH3:23])[CH:22]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 79493,5-DimethylanilineHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 53405864N-(3,5-dimethylphenyl)-2-(hydroxyimino)acetamideYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of chloral hydrate (14.1 g, 85.24 mM) and sodium sulfate (88.2g, 7.53 eq.) in 270 mL of water was added a solution of 3,5-dimethylaniline in a solution of concentrated HCl (16 mL) and water (51 mL), whereupon an off-white precipitate formed. The mixture was stirred for 10 min prior to adding an aqueous solution of hydroxylamine hydrochloride (17.4 g, 250 mM) in water (50 mL) and then heated at reflux for 10 min during which time the solids dissolved and a tan precipitate formed. The mixture was cooled and filtered, and the collected solids were air dried to yield the title compound (15.0 g, 95%).

Workup

  1. customwhereupon an off-white precipitate formed
  2. temperatureheated
  3. temperatureat reflux for 10 min during which time the solids
  4. dissolutiondissolved
  5. customa tan precipitate formed
  6. temperatureThe mixture was cooled
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-5139598c1f4b45d2b198d2ebd6c62ba7
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Linked notes

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