Pyridine → HCID 14204773, compound

HRID 1742059Notes

Reaction equation

C(#N)C.[CH3:4][S:5]([OH:8])(=[O:7])=[O:6].[F:9]F.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH3:4][S:5]([O-:8])(=[O:7])=[O:6].[F:9][N+:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Reactant 4

HCID 1049Pyridine2×

HCID 6342Acetonitrile

HCID 6395Methanesulfonic Acid2×

HCID 24524Fluorine2×

Product 1

HCID 14204773HCID 14204773, compound

Conditions

Temperature: -20 °C

Procedure

To 40 ml of acetonitrile were added 1.655 g (20.923 mmol) of pyridine and 1,961 g (20.406 mmol) of methanesulfonic acid (i.e., the amount of pyridine was 1,025 times that of methanesulfonic acid in a molar ratio), and the mixture was cooled to -20° C. A mixed gas of fluorine and nitrogen in a volumetric ratio of 1:4 was then introduced to the mixture at a rate of 50 ml/min under stirring. The amount of fluorine gas introduced was 40.0 mmol. After completion of the reaction, the solvent was distilled off, and 3,691 g ¢19.103 mmol) N-fluoropyridinium methanesulfonate was obtained by crystallizing with ether. The yield was

Workup

customAfter completion of the reaction
distillationthe solvent was distilled off

Sources & evidence

ORD record: ord-9e1ea568b7724014aa156cb79aae2239
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05336772

Reaction notes

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