Toluene → HCID 9859720, compound

HRID 1700815Notes

Reaction equation

HRID 1700815 reaction equation
O=[C:2]([CH:4]=[C:5]([CH3:7])[CH3:6])[CH3:3].[C:8]1([S:14]([C:17]#[N:18])(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(C)C=CC=CC=1.B(OCCCC)(OCCCC)OCCCC>C(O)CCC>[C:8]1([S:14]([C:17]2[CH:6]=[C:5]([CH3:7])[CH:4]=[C:2]([CH3:3])[N:18]=2)(=[O:15])=[O:16])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8858Mesityl oxideHCID 12712Tributyl borateHCID 10313279Benzenesulfonyl cyanide

Product 1

HCID 9859720HCID 9859720, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
116 °C

Procedure

First, 9.80 g (100 mmol) of mesityl oxide (4-methyl-3-penten-2-one) and 8.35 g (50.0 mmol) of benzenesulfonyl cyanide were introduced to the same reaction vessel as in Example 1. Toluene (15 ml) as the solvent and butanol (1.5 ml) were added, and 1.15 g (5.00 mmol) of tributyl borate was added. Then the mixture was heated under reflux for 10 hours while agitating at an internal temperature of 116° 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 6.14 g of 2-benzenesulfonyl-4,6-dimethylpyridine with the following properties as colorless crystals (purity of 99%, yield of 49% based on benzenesulfonyl cyanide).

Workup

  1. temperatureThen the mixture was heated
  2. temperatureunder reflux for 10 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 toluene that
  14. temperaturehad been cooled to 5° C.
  15. customThen the crystals were dried for 2 hours in vacuo

Sources & evidence

ORD record
ord-134910d692b44a54ae99c3089ff6527b
Source dataset
uspto-grants-2002_02
Patent number
US06350876B2

Reaction notes

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