Potassium Carbonate → HCID 86684081, compound

HRID 407820Notes

Reaction equation

HRID 407820 reaction equation
[N+:1]([C:4]1[CH:8]=[N:7][NH:6][N:5]=1)([O-:3])=[O:2].Cl[C:10]([F:15])([F:14])C([O-])=O.[Na+].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[F:14][CH:10]([F:15])[N:6]1[N:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2781504-nitro-2H-1,2,3-triazoleHCID 2734985Sodium chlorodifluoroacetate

Product 1

HCID 86684081HCID 86684081, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 100-mL single-neck round-bottomed flask containing 4-nitro-2H-1,2,3-triazole (500 mg, 4.38 mmol, 1.0 eq.), sodium 2-chloro-2,2-difluoroacetate (1310 mg, 8.76 mmol, 2.0 eq.), K2CO3 (1140 mg, 8.76 mmol, 2.0 eq.), and acetonitrile (20 mL) was stirred at reflux for 5 h. After cooling to room temperature, the reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 4:1 petroleum ether/ethyl acetate to afford 159a (350 mg, 48%) as a brown liquid. 1H NMR (500 MHz, CDCl3) δ 8.38 (s, 1H), 7.39 (t, J=57.5 Hz, 1H).

Workup

  1. temperatureat reflux for 5 h
  2. filtrationthe reaction mixture was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by silica-gel column chromatography
  5. washeluting with 4:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-862ed1454c474bda9314bd066dce8c46
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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