Sodium Hydroxide → N-[4-[[(Z)-(5-nitro-2-oxo-1H-indol-3-ylidene)-phenylmethyl]amino]phenyl]methanesulfonamide

HRID 24892Notes

Reaction equation

HRID 24892 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[C:6](=[C:16](OCC)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]1=[O:26])(=O)C.[CH3:27][S:28]([NH:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1)(=[O:30])=[O:29].[OH-].[Na+]>CN(C=O)C.CO>[CH3:27][S:28]([NH:31][C:32]1[CH:38]=[CH:37][C:35]([NH:36]/[C:16](=[C:6]2\[C:5](=[O:26])[NH:4][C:12]3[C:7]\2=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=3)/[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:34][CH:33]=1)(=[O:30])=[O:29]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 37325774-(Methylsulfonamido)anilineHCID 542801041-Acetyl-3-{1-ethoxy-1-phenylmethylidene}-5-nitro-2-indolinone

Product 1

HCID 178505033N-[4-[[(Z)-(5-nitro-2-oxo-1H-indol-3-ylidene)-phenylmethyl]amino]phenyl]methanesulfonamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 82 from 1-acetyl-3-(1-ethoxy-1-phenyl-methylidene)-5-nitro-2-indolinone and 4-methylsulphonylamino-aniline in DMF and subsequent treatment with sodium hydroxide solution in methanol.

Sources & evidence

ORD record
ord-20732e003ff0486a9f2034c64618fce5
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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