5-Iodoisatin → HCID 178427306, compound

HRID 642056Notes

Reaction equation

HRID 642056 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.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH2:23][C:24]([NH:26][NH2:27])=[O:25])(=[O:22])=[O:21])=[CH:16][CH:15]=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:27][NH:26][C:24](=[O:25])[CH2:23][S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:13])=[CH:15][CH:16]=1)(=[O:21])=[O:22]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 561546HCID 561546, compound

Product 1

HCID 178427306HCID 178427306, compoundYield 82%

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 2-[(4-methylphenyl)sulfonyl]acetohydrazide. 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 199 mg of the title compound (82%) as a yellow solid in 91.1% purity by HPLC (Rt: 5.38, gradient of 10 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-44349ac7fd6b468baa8bcca9ce56447e
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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