Diisopropyl Ether → 2-(Benzenesulfonyl)pyridine

Temperature

83 °C

First, 8.20 g (115 mmol) of crotonaldehyde and 9.55 g (57.2 mmol) of benzenesulfonyl cyanide were introduced to the same reaction vessel as in Example 1. Diisopropyl ether (15 ml) as the solvent and butanol (1.5 ml) were added, and 1.33 g (5.78 mmol) of tributyl borate was added. Then the mixture was heated under reflux for 20 hours while agitating at an internal temperature of 83° 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 isopropyl ether that had been cooled to 5° C. or lower. Then the crystals were dried for 2 hours in vacuo to give 11.9 g of 2-benzenesulfonylpyridine as colorless crystals (purity of 99%, yield of 94% based on benzenesulfonyl cyanide).

1. temperatureThen the mixture was heated
2. temperatureunder reflux for 20 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 isopropyl ether that
14. temperaturehad been cooled to 5° C.
15. customThen the crystals were dried for 2 hours in vacuo

ORD record

ord-9837b44b50a64c078188d6adbd123c84

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06197962B1