Picolyl chloride hydrochloride → 2-{[(2,5-Dimethylfuran-3-yl)sulfanyl]methyl}pyridine

HRID 1288615노트

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HRID 1288615 반응식
C[O-].[Na+].[CH3:4][C:5]1[O:6][C:7]([CH3:11])=[CH:8][C:9]=1[SH:10].Cl.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19]Cl>CO>[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][S:10][C:9]1[CH:8]=[C:7]([CH3:11])[O:6][C:5]=1[CH3:4]

참가 물질

5

반응물 3

HCID 23392Picolyl chloride hydrochlorideHCID 415692,5-Dimethyl-3-furanthiolHCID 10942334Sodium Methoxide

생성물 1

HCID 215030872-{[(2,5-Dimethylfuran-3-yl)sulfanyl]methyl}pyridine

시약·촉매·용매 1

HCID 887Methanol용매3회

반응 조건

온도
25 °C

실험 절차

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 0.64 g (0.005 moles) of 2,5-dimethyl-3-furan thiol in 3 ml absolute methanol is added to the reaction mass. While maintaining the reaction 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 allowed to cool to 25° C with stirring over a period of 30 minutes. The reaction mass 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 30° C and flushed with nitrogen. After remaining at room temperature for a period of 20 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 into 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, and concentrated on a rotary evaporator using water-aspirator vacuum.

후처리

  1. temperaturepot thermometer, Y tube, nitrogen inlet tube, reflux condenser
  2. temperatureheating mantle
  3. temperatureThe reaction mass is maintained at 25°-30° C
  4. temperatureWhile maintaining
  5. customthe reaction at 25° C
  6. additionis added to the reaction mass
  7. customwarms up to 42° C
  8. temperatureThe reaction mass is then heated
  9. temperatureto reflux (60° - 65° C) under nitrogen
  10. temperaturereflux
  11. waitis continued for a period of 1 hour
  12. temperatureThe reaction mass is cooled to 30° C
  13. customflushed with nitrogen
  14. waitAfter remaining at room temperature for a period of 20 hours
  15. additionof water is added to the reaction mass
  16. stirringwith stirring
  17. addition7 ml of n-hexane is then added to the reaction mass
  18. stirringwith stirring
  19. customtransferred into a separatory funnel
  20. customThe aqueous layer is separated from the organic phase
  21. extractionextracted with 8 ml n-hexane
  22. additionafter first diluting the aqueous phase with another 10 ml of water
  23. washwashed with 7 ml of saturated sodium chloride solution
  24. dry with materialdried over anhydrous sodium sulfate, gravity
  25. filtrationfiltered
  26. concentrationconcentrated on a rotary evaporator

출처 및 근거

ORD 기록
ord-dcb34132a3e44a73b16ee173894624da
출처 데이터셋
uspto-grants-1976_10
특허 번호
US03988510

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