Water → N-(1-benzoyl-2,3-dihydro-1H-indole-5-yl)-methanesulfonamide

HRID 1359143ノート

反応式

HRID 1359143 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[H-].[Na+].[OH2:17]>ClCCl>[C:3]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][S:11]([CH3:14])(=[O:12])=[O:13])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)(=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 962WaterHCID 24758Sodium hydrideHCID 18182841N-(2,3-Dihydro-1H-indol-5-YL)methanesulfonamide

生成物 1

HCID 9922932N-(1-benzoyl-2,3-dihydro-1H-indole-5-yl)-methanesulfonamide収率 50%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

N-(2,3-dihydro-1H-indole-5-yl)-methanesulfonamide (20 mg, 0.095 mmol) was dissolved in anhydrous dichloromethane (3 ml), sodium hydride (0.010 g, 50% in oil) was added and then, benzolychloride (0.011 ml, 0.095 mmol) was added at a temperature under −20° C. The resulting solution was stirred at the same temperature for 1 hour, stirred again at room temperature for 24 hours to complete the reaction. After pouring water (3 ml), dichloromethane layer was separated, washed with brine, dried over anhydrous magnesium sulfate and then, concentrated under reduced pressure. Afterward, the residue was purified through flash column chromatography (an eluent: ethyl acetate/n-hexane=1/1, v/v) and triturated with isooctane. As a result, the present compound (15 mg, productive yield 50%) was obtained as a solid.

後処理

  1. additionbenzolychloride (0.011 ml, 0.095 mmol) was added at a temperature under −20° C
  2. stirringstirred again at room temperature for 24 hours
  3. customthe reaction
  4. customwas separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customAfterward, the residue was purified through flash column chromatography (an eluent
  9. customethyl acetate/n-hexane=1/1, v/v) and triturated with isooctane
  10. customAs a result, the present compound (15 mg, productive yield 50%) was obtained as a solid

出典と根拠

ORDレコード
ord-ed162bd852f940d694f6215d2011d14c
出典データセット
uspto-grants-2003_07
特許番号
US06599929B2

反応ノート

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