4-Methoxy-2-nitrobenzenesulphonyl chloride → 3-Amino-5-chloro-3-(2-chlorophenyl)-1,3-dihydro-1-(4-methoxy-2-nitrobenzenesulfonyl)indol-2-one

HRID 234526Notes

Reaction equation

HRID 234526 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].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[C:24]([N+:32]([O-:34])=[O:33])[CH:23]=1.CCCCCC.CCOC(C)=O>C(Cl)Cl>[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:28]([C:25]2[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][C:24]=2[N+:32]([O-:34])=[O:33])(=[O:29])=[O:30])[C:3]1=[O:12]

Participants

5

Reactant 3

HCID 874524-Methoxy-2-nitrobenzenesulphonyl chlorideHCID 190763763-Amino-5-chloro-3-(2-chlorophenyl)-1,3-dihydroindol-2-oneHCID 21226206Ethyl acetate hexane

Product 1

HCID 190763693-Amino-5-chloro-3-(2-chlorophenyl)-1,3-dihydro-1-(4-methoxy-2-nitrobenzenesulfonyl)indol-2-oneYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound is prepared according to the procedure described in EXAMPLE 1 from 2 g of 3-amino-5-chloro-3-(2-chlorophenyl)-1,3-dihydroindol-2-one and 1.71 g of 4-methoxy-2-nitrobenzenesulfonyl chloride. Chromatography on silica using a DCM/hexane mixture (80/20; v/v) and then DCM as the eluent gives 2.8 g of the expected product after crystallization from a DCM/iso ether mixture. M.p.=192°-195° C.

Workup

  1. customThis compound is prepared

Sources & evidence

ORD record
ord-e0aea322e42448f881e0e2e4b5e997fc
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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