Benzenesulfonyl chloride → N-(5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)benzenesulfonamide

HRID 492082

반응식

HRID 492082 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1.O>[O:12]=[C:8]1[CH2:7][CH2:6][CH2:5][C:4]2[CH:3]=[C:2]([NH:1][S:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)(=[O:21])=[O:20])[CH:11]=[CH:10][C:9]1=2

참가 물질

5

반응물 2

HCID 7369Benzenesulfonyl chlorideHCID 3395376-Amino-1,2,3,4-tetrahydronaphthalen-1-one

생성물 1

HCID 68830588N-(5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)benzenesulfonamide

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

반응 조건

온도
23 °C

실험 절차

To a solution of 0.46 gram (2.85 mmole) 6-amino-3,4-dihydro-2H-naphthalen-1-one in 25 mL pyridine was added 0.605 grams (3.42 mmoles) benzenesulfonyl chloride. The reaction mixture was stirred at 23° C. for 24 hours. The mixture was diluted with 100 mL water and extracted with 200 mL ethyl acetate. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to low pressure column chromatography over silica gel 230-400 mesh eluting with 50% ethyl acetate in hexane. The title compound was obtained as a solid, 0.48 gram (56%), m.p. 164-165° C., M−H=300.

후처리

  1. extractionextracted with 200 mL ethyl acetate
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. washeluting with 50% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-f9260c5fe5154020ab983ebb14106707
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531577B2

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