Ethanol → HCID 9920800, compound

HRID 270185Notes

Reaction equation

HRID 270185 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]2[C:7]3=[CH:11][S:12][C:13]([N:14]4C(=O)C5C(=CC=CC=5)C4=O)=[C:6]3[C:5](=[O:25])[C:4]=2[CH:3]=1.O.NN.[CH2:29](O)C>>[NH2:14][C:13]1[S:12][CH:11]=[C:7]2[C:8]3[C:9]([CH3:29])=[CH:10][CH:2]=[CH:3][C:4]=3[C:5](=[O:25])[C:6]=12

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 21964345HCID 21964345, compound

Product 1

HCID 9920800HCID 9920800, compound

Procedure

To a suspension of 2-(6-chloro-8-oxo-8H-2-thia-cyclopenta[a]inden-1-yl)-isoindole-1,3-dione (0.45 mmol, Example 10, Part E) in absolute ethanol (5 mL) is added hydrazine hydrate (0.5 mmol). The mixture is heated to reflux for one hour, cooled to room temperature, concentrated in vacuo, and the residue dissolved in methylene chloride. The solution is chilled to 5° C. for one hour, during which time the phthaloyl hydrazide precipitates. The precipitate is removed by filtration, the filtrate concentrated in vacuo, and the residue purified by column chromatography on silica gel, eluting with a 4:1 mixture of petroleum ether:ethyl acetate. Fractions containing the product are collected, evaporated, and the product recrystallized.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for one hour
  3. concentrationconcentrated in vacuo
  4. dissolutionthe residue dissolved in methylene chloride
  5. temperatureThe solution is chilled to 5° C. for one hour, during which time the phthaloyl hydrazide
  6. customprecipitates
  7. customThe precipitate is removed by filtration
  8. concentrationthe filtrate concentrated in vacuo
  9. customthe residue purified by column chromatography on silica gel
  10. washeluting with a 4:1 mixture of petroleum ether
  11. additionFractions containing the product
  12. customare collected
  13. customevaporated
  14. customthe product recrystallized

Sources & evidence

ORD record
ord-2de51ddb83d94edaae6439472aedf898
Source dataset
uspto-grants-2008_11
Patent number
US07449490B2

Reaction notes

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