Reaktion #2254163

Reaktionsgleichung

2,2,2-trifluoroethyl trifluoromethanesulfonate

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

2,2,2-trifluoroethyl trifluoromethanesulfonate

sodium hydride

potassium carbonate

→

title compound

Ausbeute 132.6%

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

Ausbeute 132.6%

Lösungsmittel

water

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to 0° C
2. 2
   workup.STIRRINGStirring
3. 3
   workup.WAITwas conducted at room temperature for 2 hours
4. 4
   ExtraktionExtraction with ethyl acetate
5. 5
   SonstigeThe organic layer obtained
6. 6
   Waschenwas washed with a saturated aqueous sodium chloride solution
7. 7
   Trocknendried over anhydrous magnesium sulfonate
8. 8
   Filtrationfiltered
9. 9
   Sonstigeto remove inorganic matter
10. 10
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure
11. 11
    SonstigeThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

Vorschrift

1.81 g (7.81 mM) of 2,2,2-trifluoroethyl trifluoromethanesulfonate was added to an N,N-dimethylformamide solution (20 ml) of 1.00 g (7.81 mM) of 3-amino-2,3-bis(hydroxyimino)propionitrile. The mixture was cooled to 0° C. Thereto was added 1.08 g (7.81 M) of potassium carbonate. Stirring was conducted at room temperature for 3 hours. The mixture was cooled to 0° C. Thereto were added 1.81 g (7.81 mM) of 2,2,2-trifluoroethyl trifluoromethanesulfonate and 0.34 g (7.8 mM) of 55% sodium hydride. Stirring was conducted at room temperature for 2 hours. The reaction mixture was poured into water. Extraction with ethyl acetate was conducted. The organic layer obtained was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfonate, 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 acetate:hexane=1:2) to obtain 1.51 g (yield: 66%) of the title compound.

Quelle