Water → HCID 66687566, compound

HRID 1428652Notes

Reaction equation

HRID 1428652 reaction equation
[Cl:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]2[O:6][C@H:7]([CH2:10]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:8][O:9][C:4]=2[CH:3]=1.[C:25]1(=[O:35])[NH:29][C:28](=[O:30])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]12.[K].O>CN(C=O)C>[Cl:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]2[O:6][C@@H:7]([CH2:10][N:29]3[C:25](=[O:35])[C:26]4[C:27](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:28]3=[O:30])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24194345Phthalimide potassium saltHCID 86602261HCID 86602261, compound

Product 1

HCID 66687566HCID 66687566, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Toluene-4-sulfonic acid (2S)-6,7-dichloro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester (8.0 g, 20.5 mmol) was combined with potassium phthalimide (6.1 g, 33 mmol) in DMF (75 mL) and heated to reflux for 1 h, cooled to room temperature and poured into vigorously stirring water (0.5 L) and then stirred 30 min. White solid was filtered and the solid was washed several times with water, 2% NaOH, and water again and then let air dry to yield (2S)-2-(6,7-dichloro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-isoindole-1,3-dione (6.0 g, 80%) as a white powdery solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. filtrationWhite solid was filtered
  4. washthe solid was washed several times with water, 2% NaOH, and water again
  5. customdry

Sources & evidence

ORD record
ord-94276e4962e14638afd7866f4deab64a
Source dataset
uspto-grants-2015_01
Patent number
US08937096B2

Reaction notes

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