5-Iodoisatin → HCID 178517222, compound

HRID 642136Notes

Reaction equation

HRID 642136 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.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:23][NH2:24])(=[O:22])=[O:21])=[CH:16][C:15]=1[N+:25]([O-:27])=[O:26]>C(O)(=O)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:23][N:24]=[C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=3)[NH:7][C:6]2=[O:11])(=[O:22])=[O:21])=[CH:16][C:15]=1[N+:25]([O-:27])=[O:26]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 27742144-Chloro-3-nitrobenzenesulfonohydrazide

Product 1

HCID 178517222HCID 178517222, compoundYield 77%

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 4-chloro-3-nitrobenzenesulfonohydrazide. 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 78 mg of the title compound (77%) as a yellow solid in 73% purity by HPLC (Rt: 3.65, 5.39, 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-f7b65f3197f341a7a86a927eeccedf57
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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