5-Iodoisatin → HCID 178517189, compound

HRID 642048Notes

Reaction equation

HRID 642048 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[O:14][N:15]=[C:16]2[CH:21]=[C:20]([C:22]([NH:24][NH2:25])=[O:23])[CH:19]=[CH:18][C:17]=12>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:25][NH:24][C:22]([C:20]1[CH:19]=[CH:18][C:17]2=[N:13][O:14][N:15]=[C:16]2[CH:21]=1)=[O:23]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 27354552,1,3-benzoxadiazole-5-carbohydrazide

Product 1

HCID 178517189HCID 178517189, 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 2,1,3-benzoxadiazole-5-carbohydrazide. 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 166 mg of the title compound (77%) as a orange solid in 99.1% purity by HPLC (Rt: 5.65, 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-48bc710da51b44988d790092b633c771
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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