Dimethyl Sulfoxide → Pyridine, 3-chloro-2-[(phenylmethyl)thio]-

HRID 847124Notes

Reaction equation

HRID 847124 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[CH2:19]([SH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[CH2:19]([S:26][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 169882,3-Dichloropyridine

Product 1

HCID 19881832Pyridine, 3-chloro-2-[(phenylmethyl)thio]-Yield 78.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 g of 2,3-dichloropyridine, 11.2 g of anhydrous potassium carbonate and 100 ml of dimethylsulfoxide were mixed to obtain a suspension. To this suspension, 10 ml of a dimethylsulfoxide solution of 10.1 g of benzyl mercaptan was dropwise added over a period of about 20 minutes at 110° C. Then, the mixture was reacted at a temperature of from 120 to 130° C. for about 1.5 hours. Thereafter, the reaction product was put into water and extracted with methylene chloride. The methylene chloride layer was dried over anhydrous sodium sulfate. Then, methylene chloride was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 12.5 g of oily 2-benzylthio-3-chloropyridine.

Workup

  1. customto obtain a suspension
  2. customThen, the mixture was reacted at a temperature of from 120 to 130° C. for about 1.5 hours
  3. extractionextracted with methylene chloride
  4. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  5. distillationThen, methylene chloride was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6682ecc6a224494b8df2baba399919ba
Source dataset
uspto-grants-1992_08
Patent number
US05139565

Reaction notes

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