Tributyl borate → 2-Benzenesulfonyl-4-phenylpyridine

HRID 1531383

Reaction equation

HRID 1531383 reaction equation
[C:1]1([C:7]([CH3:11])=[CH:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]1([S:18]([C:21]#[N:22])(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.B(OCCCC)(OCCCC)OCCCC>>[C:12]1([S:18]([C:21]2[CH:11]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:8]=[CH:9][N:22]=2)(=[O:19])=[O:20])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 12712Tributyl borateHCID 145283-Phenyl-2-butenalHCID 10313279Benzenesulfonyl cyanide

Product 1

HCID 98391092-Benzenesulfonyl-4-phenylpyridineYield 71%

Conditions

Temperature
112 °C

Procedure

First, 0.93 g (6.36 mmol) of 3-phenyl-2-butenal and 0.99 g (5.91 mmol) of benzenesulfonyl cyanide were introduced to a 3-necked flask (25 ml volume) equipped with a thermometer, a magnetic stirrer, a Dean-Stark water type distilling receiver, and a condenser tube. Toluene (5 ml) as the solvent and butanol (0.5 ml) were added, and 0.14 g (0.59 mmol) of tributyl borate was added. Then the mixture was heated under reflux for 2 hours while agitating at an internal temperature of 112° 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 to give the desired, crude product. The crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=¼) to give 1.20 g of 2-benzenesulfonyl-4-phenylpyridine with the following properties as colorless crystals (purity of 99%, yield of 71% 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 (5 ml) as the solvent and butanol (0.5 ml) were added
  4. temperatureThen the mixture was heated
  5. temperatureunder reflux for 2 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. customto give the
  12. customThe crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=¼)

Sources & evidence

ORD record
ord-ea3f4e005a0840acb2085ad6b94515d1
Source dataset
uspto-grants-2001_03
Patent number
US06197962B1

Linked notes

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