Water → 2-[(4-nitrophenyl)methylsulfanyl]pyridine

HRID 856665Notes

Reaction equation

HRID 856665 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1)([O-:17])=[O:16].O>C1COCC1>[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22][S:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromideHCID 178418616HCID 178418616, compound

Product 1

HCID 6770632-[(4-nitrophenyl)methylsulfanyl]pyridineYield 76.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-mercaptopyridine (2.6 g) was dissolved in THF (52 ml), triethylamine (3.9 ml) was added to the mixture, and then, a solution of 4-nitrobenzyl bromide (4.8 g) in. THF (24 ml) was added dropwise to the mixture. The reaction solution was stirred for 30 minutes at room temperature, 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. The obtained residue was purified by silica gel column chromatography, to give 2-[(4-nitrobenzyl)sulfanyl]pyridine (4.2 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c8bbdf1f094d4d0c88646403a2ede63d
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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