Diethylene Glycol → 2-[2-(2-Hydroxyethoxy)ethoxy]-1H-isoindole-1,3(2H)-dione

HRID 1506615Notes

Reaction equation

[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C1CCN2C(=NCCC2)CC1.CC1C=CC(S([O-])(=O)=O)=CC=1.[CH2:35]([OH:41])[CH2:36][O:37][CH2:38][CH2:39]O>CN(C=O)C>[OH:41][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of N-hydroxyphtalimide (4.3 g, 26.2 mmol) in dry DMF (mL) was added DBU (4.0 g, 26.2 mmol). To this dark red solution was added monotosylate of diethylene glycol (6.8 g, 26.2 mmol). The reaction mixture was heated at 80° C. overnight, concentrated in vacuo, dissolved in ethyl acetate (200 mL) and extracted with saturated sodium bicarbonate until the aqueous phase was colorless. The organic phase was evaporated and dried by coevaporation with toluene. The title product was obtained after purification by flash silica gel chromatography as white solid. Yield 74%.

Workup

concentrationconcentrated in vacuo
dissolutiondissolved in ethyl acetate (200 mL)
extractionextracted with saturated sodium bicarbonate until the aqueous phase
customThe organic phase was evaporated
dry with materialdried by coevaporation with toluene

Sources & evidence

ORD record: ord-8d54c37c46df4f889f1de7bbe87aac4c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09220789B2

Reaction notes

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