Reaction #3203

Reaction equation

chloral hydrate

sodium sulfate

3,5-dimethylaniline

HCl

hydroxylamine hydrochloride

→

title compound

Yield 95.0%

N-(3,5-dimethylphenyl)-2-(hydroxyimino)acetamide

Yield 95.0%

Solvents

water

water

water

Conditions

Workup

1. 1
   Otherwhereupon an off-white precipitate formed
2. 2
   Temperatureheated
3. 3
   Temperatureat reflux for 10 min during which time the solids
4. 4
   workup.DISSOLUTIONdissolved
5. 5
   Othera tan precipitate formed
6. 6
   TemperatureThe mixture was cooled
7. 7
   Filtrationfiltered
8. 8
   Otherdried

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%).

Source