4-Nitrobenzenesulfonyl chloride → 5-Chloro-3-(2-chlorophenyl)-1,3-dihydro-3-(methylamino)-1-(4-nitrobenzenesulfonyl)indol-2-one

HRID 234531Notes

Reaction equation

HRID 234531 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:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[NH:12][CH3:13].[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)([O-:23])=[O:22]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:30]([C:27]1[CH:26]=[CH:25][C:24]([N+:21]([O-:23])=[O:22])=[CH:29][CH:28]=1)(=[O:31])=[O:32])[C:6](=[O:11])[C:5]2([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[NH:12][CH3:13]

Participants

4

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 190765105-Chloro-3-(2-chlorophenyl)-1,3-dihydro-3-(methylamino)indol-2-one

Product 1

HCID 190765815-Chloro-3-(2-chlorophenyl)-1,3-dihydro-3-(methylamino)-1-(4-nitrobenzenesulfonyl)indol-2-oneYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound is prepared according to the procedure described in EXAMPLE 11 from 7.03 g of 5-chloro-3-(2-chlorophenyl)-1,3-dihydro-3-(methylamino)indol-2-one and 5.73 g of 4-nitrobenzenesulfonyl chloride. Chromatography on silica using DCM as the eluent gives 7.76 g of the expected product after crystallization from iso ether. M.p.=220°-221° C.

Workup

  1. customThis compound is prepared

Sources & evidence

ORD record
ord-5d7a58f75d6b4a79ab510a7696e7385d
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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