Potassium Carbonate → HCID 131732892, compound

HRID 2166981Notes

Reaction equation

HRID 2166981 reaction equation
FC(F)(F)S([O:6][CH2:7][C:8]([F:11])([F:10])[F:9])(=O)=O.[NH2:14][C:15](=[N:21]O)[C:16](=[N:19]O)[C:17]#[N:18].[C:23](=[O:26])([O-])[O-].[K+].[K+].[H-].[Na+]>O.CN(C)C=O>[NH2:14][C:15](=[N:21][O:6][CH2:7][C:8]([F:9])([F:10])[F:11])[C:16](=[N:19][O:26][CH2:23][C:8]([F:11])([F:10])[F:9])[C:17]#[N:18]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate2×HCID 137121577HCID 137121577, compound

Product 1

HCID 131732892HCID 131732892, compoundYield 132.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

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.

Workup

  1. temperatureThe mixture was cooled to 0° C
  2. stirringStirring
  3. waitwas conducted at room temperature for 2 hours
  4. extractionExtraction with ethyl acetate
  5. customThe organic layer obtained
  6. washwas washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfonate
  8. filtrationfiltered
  9. customto remove inorganic matter
  10. distillationThe solvent was distilled off under reduced pressure
  11. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-f2e3b6d2b77a4c8697818aad1b896b92
Source dataset
uspto-grants-2015_06
Patent number
US09044013B2

Reaction notes

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