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

HRID 492082ノート

反応式

HRID 492082 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1049Pyridine溶媒

反応条件

温度
23 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f9260c5fe5154020ab983ebb14106707
出典データセット
uspto-grants-2009_05
特許番号
US07531577B2

反応ノート

読み込み中…