Water → 4-Methylpyridine-2-sulfonyl fluoride

HRID 2047904

반응식

HRID 2047904 반응식
C([S:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1.[OH2:16].ClN1C(=[O:23])CCC1=O.[F-:25].[K+]>C(O)(=O)C>[CH3:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([S:8]([F:25])(=[O:23])=[O:16])[CH:14]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 31398ChlorosuccinimideHCID 522689Potassium FluorideHCID 583498362-(Benzylthio)-4-methylpyridine

생성물 1

HCID 583498404-Methylpyridine-2-sulfonyl fluoride

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of 2-(benzylsulfanyl)-4-methylpyridine (1.40 g) in acetic acid (10 mL)-water (5 mL) was added N-chlorosuccinimide (3.48 g) under ice-cooling, and the mixture was gradually warmed to room temperature and stirred for 4 hr. Potassium fluoride (379 mg) was added at room temperature and the mixture was stirred for 18 hr. The reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate solution. The separated aqueous layer was extracted with ethyl acetate. Combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→1:1) to give the title compound as a crude pale-yellow oil (yield 343 mg, 30%).

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred for 18 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiondiluted with ethyl acetate
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution
  6. extractionThe separated aqueous layer was extracted with ethyl acetate
  7. washCombined organic layers were washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→1:1)

출처 및 근거

ORD 기록
ord-3d51697c6b4e42d4a72432e7b333bf54
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592597B2

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