5-Iodoisatin → HCID 178520376, compound

HRID 642095Notes

Reaction equation

HRID 642095 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.[C:13]1([C:19]2[N:20]=[C:21]3[S:26][CH:25]=[C:24]([CH2:27][C:28]([NH:30][NH2:31])=[O:29])[N:22]3[N:23]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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:31][NH:30][C:28](=[O:29])[CH2:27][C:24]1[N:22]2[N:23]=[C:19]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:20]=[C:21]2[S:26][CH:25]=1

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 2743274HCID 2743274, compound

Product 1

HCID 178520376HCID 178520376, compoundYield 48%

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-(2-phenyl[1,3]thiazolo[3,2-b][1,2,4]triazol-6-yl)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 28 mg of the title compound (48%) as a yellow powder in 94.7% purity by HPLC (Rt: 4.65, 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-a5b75607de324f559062ce3c91117cb7
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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