5-Iodoisatin → HCID 178503235, compound

HRID 642060

Reaction equation

HRID 642060 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][S:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([NH:21][NH2:22])=[O:20])=[CH:17][CH:16]=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:22][NH:21][C:19](=[O:20])[C:18]1[CH:17]=[CH:16][C:15]([S:14][CH3:13])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 2654354-Methylsulfanylbenzohydrazide

Product 1

HCID 178503235HCID 178503235, compoundYield 94%

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-(methylsulfanyl)benzohydrazide. 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 411 mg of the title compound (94%) as a yellow solid in 99.3% purity by HPLC (Rt: 5.75, 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-b9569b4f053041d6939f94cc50d9bd05
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Linked notes

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