Sodium Hydroxide → 5-Nitro-2-[(2-pyridinylmethyl)sulfanyl]pyridine

HRID 856709Notes

Reaction equation

HRID 856709 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([SH:10])=[N:8][CH:9]=1)([O-:3])=[O:2].[OH-].[Na+].Cl.Cl[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1>CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 178526723C5H4N2O2S

Product 1

HCID 695219185-Nitro-2-[(2-pyridinylmethyl)sulfanyl]pyridineYield 65.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-nitro-2-pyridinethiol (6.0 g) was dissolved in an aqueous solution of methanol (150 ml), and to this solution was added sodium hydroxide (4.6 g) and then, 2-(chloromethyl)pyridine hydrochloride (7.6 g), and the mixture was stirred for 15 minutes at room temperature. The solvent was removed under reduced pressure, and water was added to the obtained residue, and the mixture 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 5-nitro-2-[(2-pyridinylmethyl)sulfanyl]pyridine (6.2 g).

Workup

  1. customThe solvent was removed under reduced pressure, and water
  2. additionwas added to the obtained residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b3cb816f83244be2a86eb2926e68738b
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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