Dimethyl Sulfoxide → HCID 13788291, compound

HRID 847125Notes

Reaction equation

HRID 847125 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[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[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[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 876016-Chloro-2-picoline

Product 1

HCID 13788291HCID 13788291, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.8 g of 2-chloro-6-methylpyridine, 18 g of anhydrous potassium carbonate and 100 ml of dimethylsulfoxide were mixed to obtain a suspension. This suspension was preliminarily heated to a temperature of from 120° to 130° C., and 10 ml of a dimethylsulfoxide solution of 18.6 g of benzyl mercaptan was dropwise added thereto over a period of about 30 minutes. Then, the mixture was reacted at 150° C. for about one hour. Thereafter, the reaction solution was cooled, then put into water and extracted with methylene chloride. The methylene chloride layer was dried over anhydrous sodium sulfate, and then methylene chloride was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 7.53 g of oily 2-benzylthio-6-methylpyridine.

Workup

  1. customto obtain a suspension
  2. additionwas dropwise added
  3. customThen, the mixture was reacted at 150° C. for about one hour
  4. temperatureThereafter, the reaction solution was cooled
  5. extractionextracted with methylene chloride
  6. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  7. distillationmethylene chloride was distilled off under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7cf81faceb6345c49daf92f796885506
Source dataset
uspto-grants-1992_08
Patent number
US05139565

Reaction notes

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