Tributyl borate → 2-Benzenesulfonyl-4-methyl-6-phenylpyridine

HRID 1531382Notes

Reaction equation

HRID 1531382 reaction equation
[CH3:1][C:2]([CH3:12])=[CH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[C:13]1([S:19]([C:22]#[N:23])(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.B(OCCCC)(OCCCC)OCCCC>>[C:13]1([S:19]([C:22]2[CH:1]=[C:2]([CH3:12])[CH:3]=[C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:23]=2)(=[O:20])=[O:21])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 12712Tributyl borateHCID 976742-Buten-1-one, 3-methyl-1-phenyl-HCID 10313279Benzenesulfonyl cyanide

Product 1

HCID 99047352-Benzenesulfonyl-4-methyl-6-phenylpyridineYield 28%

Conditions

Temperature
112 °C

Procedure

First, 0.96 g (6.00 mmol) of 3-methyl-l-phenyl-2-buten-1-one and 0.84 g (5.00 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 0.12 g (0.50 mmol) of tributyl borate was added. Then the mixture was heated under reflux for 8 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 recrystallized with 5 ml of ethyl acetate to give 0.42 g of 2-benzenesulfonyl-4-methyl-6-phenylpyridine with the following properties as colorless crystals (purity of 99%, yield of 28% 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 8 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 recrystallized with 5 ml of ethyl acetate

Sources & evidence

ORD record
ord-b9858b6e990f46ec943de11e40bd43fd
Source dataset
uspto-grants-2001_03
Patent number
US06197962B1

Reaction notes

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