Phthalimide potassium salt → 3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-propane-1-sulfonic acid dimethylamide

HRID 2098840Notes

Reaction equation

[CH3:1][N:2]([CH3:10])[S:3]([CH2:6][CH2:7][CH2:8]I)(=[O:5])=[O:4].[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K]>CN(C=O)C>[CH3:1][N:2]([CH3:10])[S:3]([CH2:6][CH2:7][CH2:8][N:15]1[C:11](=[O:21])[C:12]2[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:14]1=[O:16])(=[O:5])=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-iodo-propane-1-sulfonic acid dimethylamide (600 mg) in DMF (10 mL) was added potassium phthalimide (590 mg) and the reaction heated at 100° C. for 16 h. After cooling to room temperature, the reaction was partitioned between dichloromethane (30 mL) and water (30 mL). The organic layer was washed with aqueous brine solution (3×30 mL), dried (MgSO4) and reduced in vacuo to give 3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propane-1-sulfonic acid dimethylamide as a white solid.

Workup

temperatureAfter cooling to room temperature
customthe reaction was partitioned between dichloromethane (30 mL) and water (30 mL)
washThe organic layer was washed with aqueous brine solution (3×30 mL)
dry with materialdried (MgSO4)

Sources & evidence

ORD record: ord-63de40a3fc1d438f8ab8a3fc4036b806
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450315B2

Reaction notes

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