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

HRID 1351700Notes

Reaction equation

HRID 1351700 reaction equation
[I:1][C:2]1[C:10]2[C:9](=[O:11])[O:8][C:7](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH2:13]C(N)=O>C1(C)C(C)=CC=CC=1>[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[NH:13][C:7]2=[O:8]

Participants

4

Reactant 2

HCID 1176UreaHCID 2820713-Iodophthalic anhydride

Product 1

HCID 184075124-iodo-1H-Isoindole-1,3(2H)-dioneYield 60.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 4-iodo-2-benzofuran-1,3-dione (0.55 g, 2.01 mmol) and urea (0.24 g, 3.99 mmol) in xylene (5 mL) was heated to reflux overnight. After cooling, the solvent was removed in vacuo and the residue partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the combined organic layers washed with brine, dried over MgSO4 and concentrated in vacuo while loading onto silica. Dry flash column chromatography using 5–10% ethyl acetate/isohexane gave 4-iodo-1H-isoindole-1,3 (2H)-dione as a pale yellow solid (330 mg, 60%).

Workup

  1. temperatureto reflux overnight
  2. temperatureAfter cooling
  3. customthe solvent was removed in vacuo
  4. customthe residue partitioned between water and ethyl acetate
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe combined organic layers washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customDry flash column chromatography

Sources & evidence

ORD record
ord-407be056cc1e423784a90d646c5f9bb1
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Reaction notes

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