p-Fluoronitrobenzene → 2-[(4-Nitrophenyl)sulfanyl]pyridine

HRID 856667Notes

Reaction equation

HRID 856667 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].F[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1>CN(C=O)C>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([S:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 178418616HCID 178418616, compound

Product 1

HCID 40533372-[(4-Nitrophenyl)sulfanyl]pyridineYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-mercaptopyridine (10 g) was dissolved in DMF (100 ml), 60% sodium hydride (3.6 g) was added to the mixture at 0° C., and then, the mixture was stirred for 15 minutes at room temperature. 4-fluoronitrobenzene (9.75 g) was added dropwise to the mixture at 0° C. and the mixture was stirred for 1 hour at room temperature. To the reaction mixture was added, and the precipitated crystals were collected by filtration, and washed with hexane/diethylether, to give 2-[(4-nitrophenyl)sulfanyl]pyridine (12.6 g).

Workup

  1. stirringthe mixture was stirred for 1 hour at room temperature
  2. additionTo the reaction mixture was added
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with hexane/diethylether

Sources & evidence

ORD record
ord-1204ce0159e044f7911bf0b6b8d71333
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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