5-Iodoisatin → HCID 178517219, compound

HRID 642057Notes

Reaction equation

HRID 642057 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.[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][S:19]([CH2:22][C:23]1[S:24][CH:25]=[C:26]([C:28]([NH:30][NH2:31])=[O:29])[N:27]=1)(=[O:21])=[O:20]>C(O)(=O)C>[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][S:19]([CH2:22][C:23]1[S:24][CH:25]=[C:26]([C:28]([NH:30][N:31]=[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:29])[N:27]=1)(=[O:20])=[O:21]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 2820012HCID 2820012, compound

Product 1

HCID 178517219HCID 178517219, compoundYield 63%

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-furylmethyl)sulfonyl]methyl}-1,3-thiazole-4-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 32 mg of the title compound (63%) as a yellow solid in 99.3% purity by HPLC (Rt: 4.8, 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-ff39204bc2f845b0b645cf6a33caf38e
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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