Methanol → 4-iodo-1H-Isoindole-1,3(2H)-dione

HRID 21112

Reaction equation

HRID 21112 reaction equation
[I:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:5]([O:7][C:8](=O)[C:3]=12)=[O:6].C[Si](C)(C)[NH:15][Si](C)(C)C.CO.O>CN(C=O)C>[I:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:5]([NH:15][C:8](=[O:7])[C:3]=12)=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 13838HexamethyldisilazaneHCID 2820713-Iodophthalic anhydride

Product 1

HCID 184075124-iodo-1H-Isoindole-1,3(2H)-dioneYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Iodophthalic anhydride (598 mg, 2.18 mmol) was dissolved in DMF (14 mL), and the solution was added with an aqueous solution (10 mL) of hexamethyldisilazane (HMDS) (4.6 mL, 22 mmol) and methanol (0.44 mL, 11 mmol), followed by stirring at room temperature for 18.5 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure a and the residue was purified by slurry using chloroform to obtain 3-iodophtalimide (403 mg, yield 68%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure a and the residue
  5. customwas purified by slurry

Sources & evidence

ORD record
ord-0ee272fea7cd425ebdbaa6a1eccbe4c9
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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