Ethanol → 2-[(2,5-Dimethylphenyl)methylsulfanyl]pyridine

HRID 2300995Notes

Reaction equation

HRID 2300995 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[K+].C(O)C.[CH3:13][C:14]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:15]=1[CH2:16]Cl>O>[CH3:13][C:14]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:15]=1[CH2:16][S:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 69987Benzene, 2-(chloromethyl)-1,4-dimethyl-HCID 178418616HCID 178418616, compound

Product 1

HCID 5073012-[(2,5-Dimethylphenyl)methylsulfanyl]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

A mixture of 5.6 g (0.05 mole) of 2-mercaptopyridine, 3.3 g (0.05 mole) of potassium hydroxide (85% pellets), 35 ml of ethanol and 5 ml of water was prepared. To this mixture was added 7.8 g (0.05 mole) of 2,5-dimethyl-benzylchloride, while maintaining good stirring. The mixture was stirred and heated to 40° C. for 45 minutes, cooled to room temperature, and then added to 150 ml of water. The aqueous mixture was extracted with 150 ml of diethyl ether; the ether phase washed with 150 ml of water. Finally, the ether phase was dried with anhydrous sodium sulfate. Removal of the ether left a green oil. An infrared spectrum was consistent with the structure of 2-((2,5-dimethylphenyl)methylthio) pyridine.

Workup

  1. customwas prepared
  2. temperaturewhile maintaining good stirring
  3. temperaturecooled to room temperature
  4. extractionThe aqueous mixture was extracted with 150 ml of diethyl ether
  5. washthe ether phase washed with 150 ml of water
  6. dry with materialFinally, the ether phase was dried with anhydrous sodium sulfate
  7. customRemoval of the ether
  8. waitleft a green oil

Sources & evidence

ORD record
ord-ffe6982de5364bfe97051376edba3789
Source dataset
uspto-grants-2002_12
Patent number
US06498254B1

Reaction notes

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