Réaction #2254163

Équation de réaction

2,2,2-trifluoroethyl trifluoromethanesulfonate

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

2,2,2-trifluoroethyl trifluoromethanesulfonate

sodium hydride

potassium carbonate

→

title compound

Rendement 132.6%

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

Rendement 132.6%

Solvants

water

N,N-dimethylformamide

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source