Water → 2-{[(2-Methylfuran-3-yl)sulfanyl]methyl}pyridine

HRID 1287938Notes

Reaction equation

HRID 1287938 reaction equation
C[O-].[Na+].[CH3:4][C:5]1[O:6][CH:7]=[CH:8][C:9]=1[SH:10].Cl.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18]Cl.O>CO.CCCCCC>[CH3:4][C:5]1[O:6][CH:7]=[CH:8][C:9]=1[S:10][CH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 23392Picolyl chloride hydrochlorideHCID 342862-Methyl-3-furanthiolHCID 10942334Sodium Methoxide

Product 1

HCID 215030882-{[(2-Methylfuran-3-yl)sulfanyl]methyl}pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
25 °C

Procedure

Into a 25 ml 3 neck round bottom flask equipped with magnetic stirrer, pot thermometer, Y tube, nitrogen inlet tube, reflux condenser and heating mantle is placed a solution of 0.54 g (0.01 moles) of sodium methoxide dissolved in 3 ml absolute methanol. The reaction mass is maintained at 25° -30° C and a solution of 0.57 g (0.005 moles) of 2-methyl-3-furan thiol in 3 ml absolute methanol is added to the reaction mass. While maintaining the reaction mass at 25° C, picolyl chloride hydrochloride (0.82 g; 0.005 moles) dissolved in 2 ml absolute methanol is added to the reaction mass. The reaction being exothermic, the reaction mass warms up to 42° C and a white solid precipitate forms. The reaction mass is then allowed to cool to 25° C (with stirring) over a period of 30 minutes. The reaction is then heated to reflux (60° - 65° C) under nitrogen and reflux is continued for a period of 1 hour. The reaction mass is cooled to 25° C. After remaining at room temperature for a period of 12 hours, 10 ml of water is added to the reaction mass with stirring, causing the reaction mass to now exist in two phases; an aqueous phase and an organic phase. The pH of the reaction mixture is 5. 7 ml of n-hexane is then added to the reaction mass with stirring and transferred to a separatory funnel. The aqueous layer is separated from the organic phase and extracted with 8 ml n-hexane after first diluting the aqueous phase with another 10 ml of water. The hexane extracts are combined, washed with 7 ml of saturated sodium chloride solution, dried over anhydrous sodium sulfate, gravity filtered, then concentrated on a rotary evaporator using water-aspirator vacuum.

Workup

  1. temperaturepot thermometer, Y tube, nitrogen inlet tube, reflux condenser
  2. temperatureheating mantle
  3. temperatureThe reaction mass is maintained at 25° -30° C
  4. additionis added to the reaction mass
  5. customwarms up to 42° C
  6. temperatureto cool to 25° C
  7. temperatureThe reaction is then heated
  8. temperatureto reflux (60° - 65° C) under nitrogen
  9. temperaturereflux
  10. waitis continued for a period of 1 hour
  11. temperatureThe reaction mass is cooled to 25° C
  12. waitAfter remaining at room temperature for a period of 12 hours
  13. stirringwith stirring
  14. stirringwith stirring
  15. customtransferred to a separatory funnel
  16. customThe aqueous layer is separated from the organic phase
  17. extractionextracted with 8 ml n-hexane
  18. additionafter first diluting the aqueous phase with another 10 ml of water
  19. washwashed with 7 ml of saturated sodium chloride solution
  20. dry with materialdried over anhydrous sodium sulfate, gravity
  21. filtrationfiltered
  22. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-0dcf328492f44b1abc87b84d5d511b0c
Source dataset
uspto-grants-1976_10
Patent number
US03985908

Reaction notes

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