Water → 2-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]acetamide

HRID 1821830Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[OH:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].Br[CH2:20][C:21]([NH2:23])=[O:22].O>CN(C=O)C>[O:13]=[C:12]1[C:11]2[C:10](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9](=[O:18])[N:8]1[O:7][CH2:20][C:21]([NH2:23])=[O:22]

Participants

Conditions

Temperature: 0 °C

Procedure

Potassium carbonate (2.67 g, 19.31 mmol) was added to a solution of N-hydroxyphthalimide (3.0 g, 18.39 mmol) in anhydrous DMF (37 mL) at 0° C. The reaction mixture was stirred at 0° C. for 10 min and then at room temperature for 1 h. The reaction mixture was cooled to 0° C. and 2-bromoacetamide (2.79 g, 20.23 mmol) was added. The reaction mixture was stirred at 0° C. for 10 min and then at room temperature overnight. The reaction mixture was poured into rapidly stirring water and the precipitated solid was collected by filtration and dried to afford 2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]acetamide (2.0 g, 49%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ4.63 (2H, s), 7.85-7.88 (4H, m); ESI MS m/z 221 [C10H8N2O4+H]+.

Workup

waitat room temperature for 1 h
temperatureThe reaction mixture was cooled to 0° C.
stirringThe reaction mixture was stirred at 0° C. for 10 min
customat room temperature
customovernight
filtrationthe precipitated solid was collected by filtration
customdried

Sources & evidence

ORD record: ord-210152f7c1cf4dd4a40d8ac58fc06c8a
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608627B2

Reaction notes

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