Réaction #2254162

Équation de réaction

potassium carbonate

2-iodopropane

N,N-dimethylformamide

3-amino-2,3-bis(hydroxyimino)propionitrile

→

3-amino-3-hydroxyimino-2-isopropoxyiminopropionitrile

Rendement 53.9%

Solvants

water

Conditions de réaction

Traitement

1. 1
   Extractionfollowed by extraction with ethyl acetate
2. 2
   AutreThe organic layer obtained
3. 3
   Lavagewas washed with a saturated aqueous sodium chloride solution
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Autreto remove inorganic matter
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
8. 8
   AutreThe resulting residue was purified by silica gel column chromatography (ethyl acetete:hexane=1:2)

Mode opératoire

2.52 g (14.8 mM) of 2-iodopropane was added to an N,N-dimethylformamide solution (30 ml) of 2.00 g (15.6 mM) of 3-amino-2,3-bis(hydroxyimino)propionitrile. The mixture was cooled to 0° C. 2.05 g (14.8 mM) of potassium carbonate was added, followed by stirring at room temperature for 16 hours. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer obtained was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered to remove inorganic matter. The solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetete:hexane=1:2) to obtain 1.36 g (yield: 51%) of 3-amino-3-hydroxyimino-2-isopropoxyiminopropionitrile (compound No. 1-004).

Source