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Water → 5-Chloro-3-(2-chlorophenyl)-1,3-dihydro-1-[4-(1,1-dimethylpropyl)benzenesulfonyl]-3-[[2-(morpholin-4-yl)ethyl]amino]indol-2-one

HRID 234535
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HRID 234535 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27])[NH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.[H-].[Na+].[CH3:30][C:31]([C:35]1[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1)([CH3:34])[CH2:32][CH3:33].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:41]([C:38]1[CH:39]=[CH:40][C:35]([C:31]([CH3:30])([CH3:34])[CH2:32][CH3:33])=[CH:36][CH:37]=1)(=[O:43])=[O:42])[C:6](=[O:11])[C:5]2([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27])[NH:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 190765095-Chloro-3-(2-chlorophenyl)-1,3-dihydro-3-[[2-(morpholin-4-yl)ethyl]amino]indol-2-oneHCID 222819764-(2-Methylbutan-2-yl)benzene-1-sulfonyl chloride

생성물 1

HCID 190764845-Chloro-3-(2-chlorophenyl)-1,3-dihydro-1-[4-(1,1-dimethylpropyl)benzenesulfonyl]-3-[[2-(morpholin-4-yl)ethyl]amino]indol-2-one수율 29.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 1 g of 5-chloro-3-(2-chlorophenyl)-1,3-dihydro-3-[[2-(morpholin-4-yl)ethyl]amino]indol-2-one in 10 ml of DMF is cooled to 0° C. under an argon atmosphere and 0.108 g of sodium hydride as a 60% dispersion in oil is added. After stirring for 30 minutes, 0.607 g of 4-(1,1-dimethylpropyl)benzenesulfonyl chloride is added and the reaction mixture is stirred for 2 hours, the temperature being allowed to rise to RT. It is poured into water and extracted with AcOEt, the organic phase is washed with water and dried over sodium sulfate and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/AcOEt mixture (80/20; v/v) as the eluent to give 0.45 g of the expected product after crystallization from a DCM/iso ether mixture. M.p.=147° C.

후처리

  1. stirringthe reaction mixture is stirred for 2 hours
  2. customto rise to RT
  3. extractionextracted with AcOEt
  4. washthe organic phase is washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (80/20; v/v) as the eluent

출처 및 근거

ORD 기록
ord-97821cec90dd424ebf695172d0a1d62e
출처 데이터셋
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05594023

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