4-(3,3-Diethyl-ureido)-benzenesulfonyl chloride → 3-Amino-5-chloro-3-(2-chlorophenyl)-1-[4-(N',N'-diethylureido)benzenesulfonyl]-1,3-dihydroindol-2-one

HRID 234530Notes

Reaction equation

HRID 234530 reaction equation
[NH2:1][C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[NH:4][C:3]1=[O:12].[CH2:20]([N:22]([CH2:36][CH3:37])[C:23](=[O:35])[NH:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1)[CH3:21]>CCCCCC.CCOC(C)=O>[NH2:1][C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]([S:31]([C:28]2[CH:27]=[CH:26][C:25]([NH:24][C:23]([N:22]([CH2:36][CH3:37])[CH2:20][CH3:21])=[O:35])=[CH:30][CH:29]=2)(=[O:33])=[O:32])[C:3]1=[O:12]

Participants

4

Reactant 2

HCID 27582454-(3,3-Diethyl-ureido)-benzenesulfonyl chlorideHCID 190763763-Amino-5-chloro-3-(2-chlorophenyl)-1,3-dihydroindol-2-one

Product 1

HCID 178856493-Amino-5-chloro-3-(2-chlorophenyl)-1-[4-(N',N'-diethylureido)benzenesulfonyl]-1,3-dihydroindol-2-oneYield 11.9%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

This compound is prepared according to the procedure described in EXAMPLE 30 from 0.293 g of 3-amino-5-chloro-3-(2-chlorophenyl)-1,3-dihydroindol-2-one, (-) isomer, and 0.290 g of 4-(N',N'-diethylureido)benzenesulfonyl chloride. Chromatography twice on silica using a DCM/AcOEt mixture (90/10; v/v) as the eluent gives 0.065 g of the expected product after crystallization and then recrystallization from a DCM/iso ether mixture and drying at 90° C. under vacuum. αd25 =-133° (c=0.24; chloroform).

Workup

  1. customThis compound is prepared

Sources & evidence

ORD record
ord-8936e78188ff4bfc89912892f8e60e30
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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