Tributyl borate → 2-(Benzenesulfonyl)pyridine

HRID 1700804Notes

Reaction equation

HRID 1700804 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.B(OCCCC)(OCCCC)OCCCC>C1(C)C=CC=CC=1>[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

5

Reactant 3

HCID 12712Tributyl borateHCID 447466CrotonaldehydeHCID 10313279Benzenesulfonyl cyanide

Product 1

HCID 2898292-(Benzenesulfonyl)pyridineYield 86.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

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. Toluene (15 ml) was added as the solvent, and 1.33 g (5.78 mol) of tributyl borate was added. Then the mixture was heated under reflux for 3 hours while agitating at an internal temperature of 110° 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 10.9 g of 2-benzenesulfonylpyridine as colorless crystals (purity of 98%, yield of 85% based on benzenesulfonyl cyanide).

Workup

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

Sources & evidence

ORD record
ord-01b3330edc3148b8ac48718846cae737
Source dataset
uspto-grants-2002_02
Patent number
US06350876B2

Reaction notes

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