Water → 3-Methyl-2-(phenylmethylthio)-pyridine

HRID 1904528Notes

Reaction equation

HRID 1904528 reaction equation
[H-].[Na+].[CH2:3]([SH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.F[C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=1.O>CN(C)C=O>[CH3:18][C:17]1[C:12]([S:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 2427222-Fluoro-3-methylpyridine

Product 1

HCID 146531873-Methyl-2-(phenylmethylthio)-pyridineYield 122.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4.8 g (100 mmole) of sodium hydride in 50 mls of dimethylformamide was cooled to 0° and 11.6 ml (100 mmole) of benzyl mercaptan was added dropwise at 0°. After addition was complete, the reaction mixture was allowed to warm to 25° and stirred at this temperature for 1 hour. The reaction mixture was then re-cooled to 0° and 10.0 g (91 mmole) of 2-fluoro-3-methyl pyridine was added dropwise. The mixture was allowed to warm to 25° and stirred at this temperature for 18 hours. The mixture was poured into 100 mls of water and extracted twice with ethyl ether and ethylacetate. The combined organic extracts were washed with a saturated solution of sodium bicarbonate and dried over sodium sulfate. Concentration gave 24 g of a yellow oil. Flash chromatography in a 10% ethyl ether/hexanes mixture gave 6.3 g clear oil.

Workup

  1. temperaturewas cooled to 0°
  2. additionAfter addition
  3. temperatureto warm to 25°
  4. temperatureThe reaction mixture was then re-cooled to 0°
  5. temperatureto warm to 25°
  6. stirringstirred at this temperature for 18 hours
  7. extractionextracted twice with ethyl ether and ethylacetate
  8. washThe combined organic extracts were washed with a saturated solution of sodium bicarbonate
  9. dry with materialdried over sodium sulfate
  10. concentrationConcentration

Sources & evidence

ORD record
ord-bda47d963fa4458aa10cb23a06980c85
Source dataset
uspto-grants-1989_06
Patent number
US04838926

Reaction notes

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