Toluene → 2-Benzenesulfonyl-5-methylpyridine

HRID 1531377노트

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HRID 1531377 반응식
[C:1]1([S:7]([C:10]#[N:11])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]1([CH3:18])[CH:17]=CC=[CH:14][CH:13]=1.B(OCCCC)(OCCCC)OCCCC>C(O)CCC>[C:1]1([S:7]([C:10]2[CH:14]=[CH:13][C:12]([CH3:18])=[CH:17][N:11]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 1140TolueneHCID 12712Tributyl borateHCID 10313279Benzenesulfonyl cyanide

생성물 1

HCID 101308512-Benzenesulfonyl-5-methylpyridine수율 89%

시약·촉매·용매 1

HCID 2631-Butanol용매

반응 조건

온도
119 °C

실험 절차

First, 4.29 g (51.1 mmol) of tiglic aldehyde 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 6 hours while agitating at an internal temperature of 119° 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 10.5 g of 2-benzenesulfonyl-5-methylpyridine as colorless crystals (purity of 99%, yield of 89% based on benzenesulfonyl cyanide).

후처리

  1. temperatureThen the mixture was heated
  2. temperatureunder reflux for 6 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

출처 및 근거

ORD 기록
ord-987925d40ec3491dbf9f24570ddf5628
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06197962B1

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