Ethyl Acetate → HCID 18951395, compound

HRID 1492720Notes

Reaction equation

HRID 1492720 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[C:14]([S:15]([OH:18])(=[O:17])=[O:16])=[CH:13][CH:12]=[C:11]([CH3:19])[N:10]=1.[F:20]F.C(OCC)(=O)C>C(#N)C>[F:20][N+:10]1[C:11]([CH3:19])=[CH:12][CH:13]=[C:14]([S:15]([O-:18])(=[O:17])=[O:16])[C:9]=1[CH3:8]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24524Fluorine2×HCID 86748337HCID 86748337, compound

Product 1

HCID 18951395HCID 18951395, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of acetonitrile (4 ml) and 2,6-dimethylpyridine-3-sulfonic acid (410 mg, 2 mmol), triethylamine (404 mg, 4 mmol) was added at room temperature while stirring, followed by evaporation to dryness under reduced pressure to obtain 2,6-dimethylpyridine-3-sulfonic acid triethylamine salt. The triethylamine salt was dissolved in acetonitrile (4 ml). To the resulting solution cooled with a cooling bath kept at -20° C., a mixed gas of 10% fluorine/ 90% nitrogen was introduced at a flow rate of 15 ml/min. The total amount of the fluorine gas was 6 mmol. Thereafter, the nitrogen gas alone was introduced for 30 minutes. Ethyl acetate was added to the reaction mixture. The precipitated crystal was recovered by filtration to obtain N-fluoro-2,6-dimethylpyridinium-3-sulfonate (257 mg). Yield, 63%. Decomposition point, 200°-210° C.

Workup

  1. temperatureTo the resulting solution cooled with a cooling bath
  2. customkept at -20° C.
  3. additionThereafter, the nitrogen gas alone was introduced for 30 minutes
  4. filtrationThe precipitated crystal was recovered by filtration

Sources & evidence

ORD record
ord-d6c271d2975a4cb1b872ce8a4b196c8b
Source dataset
uspto-grants-1994_12
Patent number
US05374732

Reaction notes

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