Potassium Carbonate → 4-[(2-Nitrophenyl)sulfanyl]pyridine

HRID 1642265Notes

Reaction equation

HRID 1642265 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.F[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[S:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 178418431pyridine-4-thiol

Product 1

HCID 137910794-[(2-Nitrophenyl)sulfanyl]pyridineYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-mercaptopyridine (2.00 g, 18.0 mmol), 1-fluoro-2-nitrobenzene (2.54 g, 18.0 mmol) and potassium carbonate (2.49 g, 18.0 mmol) in DMF (15 mL) was stirred under reflux for 2 h. After removal of DMF, the residue was dissolved in DCM and washed with NaOH (5%, 3×20 mL) and brine. The organic layer was dried (MgSO4), filtered and evaporated. Flash Master chromatography of the crude product using DCM to DCM/MeOH 98:2 gradient as eluent gave 4-(2-nitrophenylsulfanyl)-pyridine (2.4 g, 57%) as a yellow solid, mp 119-122° C.

Workup

  1. temperatureunder reflux for 2 h
  2. customAfter removal of DMF
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with NaOH (5%, 3×20 mL) and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ec589f205f784ba0b0a07f07b3adc9aa
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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