5-Iodoisatin → HCID 178517220, compound

HRID 642135Notes

Reaction equation

HRID 642135 reaction equation
[I: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=O.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[S:23][C:22]([S:24]([NH:27][NH2:28])(=[O:26])=[O:25])=[CH:21][CH:20]=1>C(O)(=O)C>[I: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=[N:28][NH:27][S:24]([C:22]1[S:23][C:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=2)=[CH:20][CH:21]=1)(=[O:25])=[O:26]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 27372485-pyridin-2-ylthiophene-2-sulfonohydrazide

Product 1

HCID 178517220HCID 178517220, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Following the general method as outlined in Example 1, into a suspension of 5-iodo-1H-indole-2,3-dione in acetic acid was added 5-(2-pyridinyl)-2-thiophenesulfonohydrazide. After stirring at 100° C., the reaction mixture was cooled to rt and a yellow solid precipitated out. Filtration on a fritté, washing with AcOH, water and drying under vacuo at 60° C. overnight gave 23 mg of the title compound (23%) as a yellow solid in 94.8% purity by HPLC (Rt: 3.68, 5.13, gradient of 8 min, MaxPlot detection between 230 and 400 nm).

Workup

  1. temperaturethe reaction mixture was cooled to rt
  2. customa yellow solid precipitated out
  3. filtrationFiltration on a fritté
  4. washwashing with AcOH, water
  5. customdrying under vacuo at 60° C. overnight

Sources & evidence

ORD record
ord-84023cd470f9488f8210002dc18245e4
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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