Toluene → 2-Benzenesulfonyl-5-methylpyridine

HRID 1531379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1531379
[C:1]1([S:7]([C:10]#[N:11])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]1([CH3:18])[CH:17]=CC=[CH:14][CH:13]=1.B(OCCCC)(OCCCC)OCCCC>C(O)CCC>[C:1]1([S:7]([C:10]2[CH:14]=[CH:13][C:12]([CH3:18])=[CH:17][N:11]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 12712Tributyl borateHCID 10313279Benzenesulfonyl cyanide

Produkt 1

HCID 101308512-Benzenesulfonyl-5-methylpyridineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
119 °C

Versuchsvorschrift

First, 9.00 g (107 mmol) of tiglic aldehyde and 8.35 g (50.0 mmol) of benzenesulfonyl cyanide were introduced to the same reaction vessel as in Example 1. Toluene (15 ml) as the solvent and butanol (1.5 ml) were added, and 0.57 g (2.48 mmoles) of tributyl borate were added. Then the mixture was heated under reflux for 7 hours while agitating at an internal temperature of 119° C. in a nitrogen atmosphere, separating and removing water that was produced. After this solution was cooled to room temperature, the low-boiling components, such as solvent, etc., were removed under reduced pressure and the resulting concentrate was cooled in an ice bath to precipitate crystals. The crystals were filtered with a glass filter and washed with 10 ml of toluene that had been cooled to 5° C. or lower. Then the crystals were dried for 2 hours in vacuo to give 8.50 g of 2-benzenesulfonyl-5-methylpyridine as colorless crystals (purity of 99%, yield of 72% based on benzenesulfonyl cyanide).

Aufarbeitung

  1. temperatureThen the mixture was heated
  2. temperatureunder reflux for 7 hours
  3. customseparating
  4. customremoving water that
  5. customwas produced
  6. temperatureAfter this solution was cooled to room temperature
  7. customthe low-boiling components, such as solvent, etc., were removed under reduced pressure
  8. concentrationthe resulting concentrate
  9. temperaturewas cooled in an ice bath
  10. customto precipitate crystals
  11. filtrationThe crystals were filtered with a glass
  12. filtrationfilter
  13. washwashed with 10 ml of toluene that
  14. temperaturehad been cooled to 5° C.
  15. customThen the crystals were dried for 2 hours in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-378b829cb6854426918ceae30ae5d6a6
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06197962B1

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