Water → 5-Chloro-3-(ethanecarboxamido)-3-(2-chlorophenyl)-1,3-dihydro-1-(2,4-dimethoxybenzenesulfonyl)indol-2-one

HRID 234499Notes

Reaction equation

HRID 234499 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[NH2:6][C:7]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[Cl:37])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:16])[CH:14]=2)[N:9]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])(=[O:19])=[O:18])[C:8]1=[O:30].O>N1C=CC=CC=1>[Cl:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[O:28][CH3:29])(=[O:19])=[O:18])[C:8](=[O:30])[C:7]2([NH:6][C:1]([CH2:2][CH3:3])=[O:4])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[Cl:37]

Participants

5

Reactant 3

HCID 962WaterHCID 62324Propionyl chlorideHCID 152844633-Amino-5-chloro-3-(2-chlorophenyl)-1,3-dihydro-1-(2,4-dimethoxybenzenesulfonyl)indol-2-one

Product 1

HCID 190763985-Chloro-3-(ethanecarboxamido)-3-(2-chlorophenyl)-1,3-dihydro-1-(2,4-dimethoxybenzenesulfonyl)indol-2-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.08 g of propionyl chloride is added to a solution of 0.33 g of the compound obtained in EXAMPLE 3 in 3 ml of pyridine and the reaction mixture is stirred for 1 hour at RT. It is poured into water, extracted with AcOEt, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using a DCM/AcOEt mixture (98/2; v/v) as the eluent to give the expected product after crystallization from a DCM/iso ether mixture. m=0.18 g. M.p.=188° C.

Workup

  1. extractionextracted with AcOEt
  2. dry with materialdried over sodium sulfate
  3. customevaporated under vacuum
  4. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (98/2; v/v) as the eluent

Sources & evidence

ORD record
ord-745955cd0fc1478da00873203fe6ff36
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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