Sodium Azide → HCID 86678051, compound

HRID 928906Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.O>[N:19]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18])=[N+:20]=[N-:21]

Participants

Conditions

Temperature: 80 °C

Procedure

To 1 mL of DMF/H2O (v/v=9/1) was added 2-(2-(2-bromoethoxy)ethoxy)isoindoline-1,3-dione (50 mg, 0.17 mmol) and sodium azide (16.6 mg, 0.26 mmol). The mixture was heated to 80° C. overnight. Then it was allowed to cool down to room temperature and was extracted with ethyl acetate for 3 times. The combined organic layers were washed with brine and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure, the crude product was purified by silica gel column chromatography (hexanes: ethyl acetate 2:1) to afford 2-(2-(2-azidoethoxy)ethoxy)isoindoline-1,3-dione (44 mg, 0.17 mmol, 100%) as colorless oil. 1H NMR (CDCl3, 500 MHz) δ (ppm): 3.28 (t, J=4.7 Hz, 2H), 3.64 (t, J=4.8 Hz, 2H), 3.84 (t, J=3.8 Hz, 2H), 4.34 (t, J=3.9 Hz, 2H), 7.71 (dd, J=2.6, 4.7 Hz, 2H), 7.79 (dd, J=3.2, 5.0 Hz, 2H).

Workup

temperatureto cool down to room temperature
extractionwas extracted with ethyl acetate for 3 times
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous Na2SO4
customSolvent was removed under reduced pressure
customthe crude product was purified by silica gel column chromatography (hexanes: ethyl acetate 2:1)

Sources & evidence

ORD record: ord-f5454fabc2b942a398025ad586127fe0
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290791B2

Reaction notes

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