Water → HCID 19076543, compound

HRID 234496Notes

Reaction equation

HRID 234496 reaction equation
[NH2:1][C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[NH:4][C:3]1=[O:12].[H-].[Na+].[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:24]=1[S:31](Cl)(=[O:33])=[O:32].O>CN(C=O)C>[NH2:1][C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]([S:31]([C:24]2[CH:25]=[CH:26][C:27]([O:29][CH3:30])=[CH:28][C:23]=2[O:22][CH3:21])(=[O:33])=[O:32])[C:3]1=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27346262,4-Dimethoxybenzenesulfonyl chlorideHCID 19076367HCID 19076367, compound

Product 1

HCID 19076543HCID 19076543, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.3 g of 3-amino-5-chloro-1,3-dihydro-3-phenylindol-2-one in 7 ml of DMF is cooled to 0° C. under an argon atmosphere and 0.037 g of sodium hydride as an 80% dispersion in oil is added. After stirring for 20 minutes, 0.275 g of 2,4-dimethoxybenzenesulfonyl chloride is added and the reaction mixture is stirred overnight, the temperature being allowed to rise to RT. It is poured into water, extracted with AcOEt, washed with water and with a saturated solution of NaCl, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using a DCM/AcOEt mixture (95/5; v/v) as the eluent to give the expected product after crystallization from a DCM/iso ether/hexane mixture. m=0.31 g. M.p.=108°-110° C.

Workup

  1. stirringthe reaction mixture is stirred overnight
  2. customto rise to RT
  3. extractionextracted with AcOEt
  4. washwashed with water and with a saturated solution of NaCl
  5. dry with materialdried over sodium sulfate
  6. customevaporated under vacuum
  7. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (95/5; v/v) as the eluent

Sources & evidence

ORD record
ord-dcd6d8956a77418c9987f5d137615d2e
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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