Reaction #2254163

Reaction equation

2,2,2-trifluoroethyl trifluoromethanesulfonate

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

2,2,2-trifluoroethyl trifluoromethanesulfonate

sodium hydride

potassium carbonate

→

title compound

Yield 132.6%

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

Yield 132.6%

Solvents

water

N,N-dimethylformamide

Conditions

Workup

1. 1
   TemperatureThe 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
   OtherThe organic layer obtained
6. 6
   Washwas washed with a saturated aqueous sodium chloride solution
7. 7
   Dryingdried over anhydrous magnesium sulfonate
8. 8
   Filtrationfiltered
9. 9
   Otherto remove inorganic matter
10. 10
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure
11. 11
    OtherThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

Procedure

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