Water → HCID 21402685, compound

HRID 2080108Notes

Reaction equation

HRID 2080108 reaction equation
[C:1]1([S:7][C:8]2[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=2)[CH2:11][N:12]2C(=O)C3C(=CC=CC=3)C2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN.O>C(O)C>[C:1]1([S:7][C:8]2[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=2)[CH2:11][NH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 23130400HCID 23130400, compound

Product 1

HCID 21402685HCID 21402685, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(3-Phenylsulfanyl-benzyl)-isoindole-1,3-dione described in Preparation Example 94 (123 mg, 0.356 mmol) was dissolved in ethanol (3 mL), hydrazine monohydrate (518 μl, 10.7 mmol) was added at 0° C., and the solution was stirred under reflux for 2 hours. Water was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (ethyl acetate), and the title compound (75 mg, 0.35 mmol, 98%) was obtained as a colorless oil.

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionwhich was then extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by NH silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-d90ba16cd50348edbcf8767485e31db6
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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