5-Iodoisatin → HCID 178517218, compound

HRID 642094Notes

Reaction equation

HRID 642094 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.[Cl:13][C:14]1[CH:30]=[CH:29][CH:28]=[CH:27][C:15]=1[O:16][CH2:17][C:18]1[S:19][CH:20]=[C:21]([C:23]([NH:25][NH2:26])=[O:24])[N:22]=1>C(O)(=O)C>[Cl:13][C:14]1[CH:30]=[CH:29][CH:28]=[CH:27][C:15]=1[O:16][CH2:17][C:18]1[S:19][CH:20]=[C:21]([C:23]([NH:25][N:26]=[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:24])[N:22]=1

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 2743890HCID 2743890, compound

Product 1

HCID 178517218HCID 178517218, compoundYield 79%

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-chlorophenoxy)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 47 mg of the title compound (79%) as a orange powder in 98.2% purity by HPLC (Rt: 5.07, 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-9435a03b265e4a47898f492a39714d05
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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