Reaction #2254162

Reaction equation

potassium carbonate

2-iodopropane

N,N-dimethylformamide

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

→

3-amino-3-hydroxyimino-2-isopropoxyiminopropionitrile

Yield 53.9%

Solvents

water

Conditions

Workup

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

Procedure

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