Water → HCID 19076412, compound

HRID 234533Notes

Reaction equation

HRID 234533 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:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[NH:12][CH2:13][CH2:14][O:15][Si](C)(C)C.[H-].[Na+].[CH2:29]([N:31]([CH2:45][CH3:46])[C:32](=[O:44])[NH:33][C:34]1[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1)[CH3:30].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:40]([C:37]1[CH:36]=[CH:35][C:34]([NH:33][C:32]([N:31]([CH2:45][CH3:46])[CH2:29][CH3:30])=[O:44])=[CH:39][CH:38]=1)(=[O:42])=[O:41])[C:6](=[O:11])[C:5]2([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[NH:12][CH2:13][CH2:14][OH:15]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27582454-(3,3-Diethyl-ureido)-benzenesulfonyl chlorideHCID 19076413HCID 19076413, compound

Product 1

HCID 19076412HCID 19076412, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.084 g of 5-chloro-3-(2-chlorophenyl)-1,3-dihydro-3-[[2-(trimethylsilyloxy)ethyl]amino]indol-2-one in 20 ml of DMF is cooled to 0° C. under an argon atmosphere and 0.111 g of sodium hydride as a 60% dispersion in oil is added. After stirring for 25 minutes, 0.78 g of 4-(N',N'-diethylureido)benzenesulfonyl chloride is added and the reaction mixture is stirred for 3 hours at RT. It is poured into water and extracted with AcOEt, the organic phase is washed with water and with a saturated solution of NaCl and dried over sodium sulfate and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/AcOEt mixture (70/30; v/v) as the eluent to give 0.505 g of the expected product after crystallization and then recrystallization from a DCM/iso ether mixture. M.p.=192°-193° C.

Workup

  1. stirringthe reaction mixture is stirred for 3 hours at RT
  2. extractionextracted with AcOEt
  3. washthe organic phase is washed with water and with a saturated solution of NaCl
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (70/30; v/v) as the eluent

Sources & evidence

ORD record
ord-30fd6ef92c68405a9888fde5689ecbdc
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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