Sodium Hydroxide → HCID 13058686, compound

HRID 856673Notes

Reaction equation

HRID 856673 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=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>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 158094-NitrobenzenethiolHCID 23392Picolyl chloride hydrochloride

Product 1

HCID 13058686HCID 13058686, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-nitrobenzenethiol (6.0 g) was dissolved in THF (120 ml), and to the solution was 1N sodium hydroxide (120 ml) 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 the obtained residue was added to water, and 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 washed with hexane/ethyl acetate, to give 2-[[(4-nitrophenyl)sulfanyl]methyl]pyridine (6.8 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe obtained residue was added to water
  3. extractionextracted 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. washthe obtained residue was washed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-8392e16d794f43f8846712f3f79cb239
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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