Sodium hydride → HCID 44322618、化合物

HRID 2144

反応式

HRID 2144 の反応式
[C:1]1([C:7]2[NH:8][C:9]([C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([S:30](Cl)(=[O:32])=[O:31])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]>CN(C)C=O>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([S:30]([N:8]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:9]2=[O:10])(=[O:31])=[O:32])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 27528701(2H)-Isoquinolinone, 3-phenyl-

生成物 1

HCID 44322618HCID 44322618、化合物収率 46.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A solution of 3-phenylisocarbostyril (0.1 g) in N,N-dimethylformamide (2 ml) was cooled to 0° C. under an inert atmosphere. Sodium hydride (0.019 g) was added and the resulting mixture stirred at 0° C. for 5 minutes. 3,4-Dimethoxybenzenesulphonylchloride (0.107 g) was added over a 3 minute period, with continued stirring at 0° C. for a further 15 minutes. The reaction mixture was warmed to room temperature and stirred for 24 hours. The DMF was evaporated under high vacuum and the residue partitioned between ethyl acetate (2×12 ml) and water (12 ml). The combined organic phases were dried over magnesium sulphate and concentrated in vacuo to yield a yellow oil. Purification using column chromatography eluting with 50% ethyl acetate in hexane yielded an oil which was crystallized from ethyl acetate/hexane to furnish the title compound as white crystals (0.089 g).

後処理

  1. stirringwith continued stirring at 0° C. for a further 15 minutes
  2. temperatureThe reaction mixture was warmed to room temperature
  3. stirringstirred for 24 hours
  4. customThe DMF was evaporated under high vacuum
  5. customthe residue partitioned between ethyl acetate (2×12 ml) and water (12 ml)
  6. dry with materialThe combined organic phases were dried over magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. customto yield a yellow oil
  9. customPurification
  10. washeluting with 50% ethyl acetate in hexane
  11. customyielded an oil which
  12. customwas crystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-1251e1d4efb04be2a0db094b4b863a07
出典データセット
uspto-grants-1998_03
特許番号
US05728712

関連ノート

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