Thiophenol → 2-Nitro-3-(phenylthio)pyridine

HRID 335123Notes

Reaction equation

HRID 335123 reaction equation
Cl[C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:11]1([SH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[N+:8]([C:3]1[C:2]([S:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 5549883-Chloro-2-nitropyridine

Product 1

HCID 669950202-Nitro-3-(phenylthio)pyridineYield 70%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

3-chloro-2-nitropyridine (30.6 g, 193 mmol) was dissolved in DMSO (200 mL). Benzenethiol (20.7 mL, 203 mmol) was added followed by cesium carbonate (69.3 g, 212 mmol) and stirred at ambient temperature for 1.5 hours. The solution was diluted with water (750 mL) and the solids filtered. The crude material was recrystallized from EtOAc (400 mL) and with adding hexanes (1 L) to give an A-crop of 23.5 g. The filtrate was concentrated and recrystallized from EtOAc/hexanes to give 7.87 g. The solids were dried on high vacuum to provide the title compound (31.38 g, 69.8% yield).

Workup

  1. filtrationthe solids filtered
  2. customThe crude material was recrystallized from EtOAc (400 mL) and with adding hexanes (1 L)
  3. customto give an A-crop of 23.5 g
  4. concentrationThe filtrate was concentrated
  5. customrecrystallized from EtOAc/hexanes
  6. customto give 7.87 g
  7. customThe solids were dried on high vacuum

Sources & evidence

ORD record
ord-fd359042ec914b41858972d6b62fcb5c
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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