Crotonaldehyde → 2-(Benzenesulfonyl)pyridine

HRID 1531368Notes

Reaction equation

HRID 1531368 reaction equation
[CH:1](=O)/[CH:2]=[CH:3]/[CH3:4].[C:6]1([S:12]([C:15]#[N:16])(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl([O-])(=O)(=O)=O.[Li+]>>[C:6]1([S:12]([C:15]2[CH:4]=[CH:3][CH:2]=[CH:1][N:16]=2)(=[O:13])=[O:14])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 447466CrotonaldehydeHCID 10313279Benzenesulfonyl cyanideHCID 23665649Lithium perchlorate

Product 1

HCID 2898292-(Benzenesulfonyl)pyridineYield 89.7%

Conditions

Temperature
110 °C

Procedure

First, 8.05 g (113 mmol) of crotonaldehyde (2-butenal) and 9.17 g (54.9 mmol) of benzenesulfonyl cyanide were introduced to a 3-necked flask (50 ml volume) equipped with a thermometer, a magnetic stirrer, a Dean-Stark water type distilling receiver, and a condenser tube. Toluene (15 ml) as a solvent and butanol (1.5 ml) were added, and then 589 mg (5.55 mmol) of lithium perchlorate was added. Next, the mixture was heated under reflux for 15 hours while agitating at an internal temperature of 110° C. in a nitrogen atmosphere, and 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 crystal were dried for 2 hours in vacuo to give 10.8 g of 2-benzenesulfonylpyridine having the following properties as colorless crystals (purity of 99%, yield of 89% based on benzenesulfonyl cyanide).

Workup

  1. customequipped with a thermometer, a magnetic stirrer
  2. distillationa Dean-Stark water type distilling receiver, and a condenser tube
  3. additionToluene (15 ml) as a solvent and butanol (1.5 ml) were added
  4. temperatureNext, the mixture was heated
  5. temperatureunder reflux for 15 hours
  6. customseparating
  7. customremoving water that
  8. customwas produced
  9. temperatureAfter this solution was cooled to room temperature
  10. customthe low-boiling components, such as solvent, etc., were removed under reduced pressure
  11. concentrationthe resulting concentrate
  12. temperaturewas cooled in an ice bath
  13. customto precipitate crystals
  14. filtrationThe crystals were filtered with a glass
  15. filtrationfilter
  16. washwashed with 10 ml of toluene that
  17. temperaturehad been cooled to 5° C.
  18. customThen the crystal were dried for 2 hours in vacuo

Sources & evidence

ORD record
ord-0ae3acf47c9c4b0db25fcfc4725e6913
Source dataset
uspto-grants-2001_03
Patent number
US06197962B1

Reaction notes

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