Water → 4-[(Pyridin-2-yl)sulfanyl]aniline

HRID 55097Notes

Reaction equation

HRID 55097 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.O>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79772-ChloropyridineHCID 145104-Aminothiophenol2×HCID 24758Sodium hydride

Product 1

HCID 189716604-[(Pyridin-2-yl)sulfanyl]anilineYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Aminothiophenol (0.065 moles, 8.1 g) in 275 ml DMF was stirred at room temperature for 1 hr with sodium hydride (0.065 moles previously washed with hexane). 2-Chloropyridine (0.06 moles, 6.8 g) was added and the reaction mixture was stirred for 6 hr. An additional 5.2 g of 4-aminothiophenol was added and the reaction stirred at room temperature for 16 hr. Water was added and the product extracted with ethyl acetate. The solution was washed thoroughly with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with 30% ethyl acetate/hexane to yield 2-(4-aminophenylthio)pyridine 1.2 g, 10%. Mass spec (FD) 202. Calculated for C11H10N2S: C, 65.32; H, 4.98, N, 13.85 Found: C, 65.23; H, 5.09; N, 13.63.

Workup

  1. washpreviously washed with hexane)
  2. stirringthe reaction stirred at room temperature for 16 hr
  3. extractionthe product extracted with ethyl acetate
  4. washThe solution was washed thoroughly with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified by HPLC over silica gel
  8. washeluted with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-58176d6b4bae4329a383e23f632dc3f2
Source dataset
uspto-grants-1997_04
Patent number
US05624937

Reaction notes

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