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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
Notes
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Reaction equation

HRID 234535 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 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-one
Yield 29.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-97821cec90dd424ebf695172d0a1d62e
Source dataset
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05594023

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes