5-Iodoisatin → HCID 178521355, compound

HRID 642059Notes

Reaction equation

HRID 642059 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][NH:19][C:20]([NH:22][CH2:23][C:24]([NH:26][NH2:27])=[O:25])=[O:21]>C(O)(=O)C>[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][NH:19][C:20]([NH:22][CH2:23][C:24]([NH:26][N:27]=[C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=2)[NH:7][C:6]1=[O:11])=[O:25])=[O:21]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 3424921HCID 3424921, compound

Product 1

HCID 178521355HCID 178521355, compoundYield 71%

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 N-(2-furylmethyl)-N′-(2-hydrazino-2-oxoethyl)urea. 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 71 mg of the title compound (71%) as a yellow solid in 95.6% purity by HPLC (Rt: 4.26, 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-2a496dc09b2a419d9a5c4e5be788731d
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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