Calcium Chloride → 4-{[(Pyridin-2-yl)methyl]sulfanyl}aniline

HRID 856674Notes

Reaction equation

HRID 856674 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[Ca+2].[Cl-]>C(O)C>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][S:10][C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 5284359Calcium ChlorideHCID 13058686HCID 13058686, compound

Product 1

HCID 130586914-{[(Pyridin-2-yl)methyl]sulfanyl}anilineYield 66.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2-[[(4-nitrophenyl)sulfanyl]methyl]pyridine (6.7 g) were added 85% ethanol solution (203 ml), and to this mixture was added calcium chloride (1.53 g) and reduced iron (7.68 g), and the mixture was heated to reflux for 16 hours. After allowing the mixture to be cooled to room temperature, ethanol was removed under reduced pressure, and the obtained residue was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-[(2-pyridinylmethyl)sulfanyl]aniline (3.9 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 16 hours
  3. customethanol was removed under reduced pressure
  4. extractionthe obtained residue was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ef4009d31bfd4f9cbbecf771ab2eaa8c
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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