N-3-Bromopropylphthalimide → 2-(3-azidopropyl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 628685Notes

Reaction equation

HRID 628685 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[N-:16]=[N+:17]=[N-:18].[Na+].[Al]>O>[N:16]([CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2[C:7](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]1=[O:15])=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 21611N-3-BromopropylphthalimideHCID 33557Sodium AzideHCID 5359268Aluminum

Product 1

HCID 1864562-(3-azidopropyl)-2,3-dihydro-1H-isoindole-1,3-dioneYield 72.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A heavy-walled Pyrex tube was charged with a suspension of N-(3-bromopropyl)phthalimide (1.00 g, 3.72 mmol) and sodium azide (0.32 g, 4.84 mmol) in H2O (2 mL). The tube containing the resulting mixture was sealed with an aluminum crimp cap fitted with a silicon septum and then it was exposed to microwave irradiation for 30 min at a temperature of 120° C. After the irradiation, the reaction tube was cooled with high-pressure air until the temperature had fallen below 40° C. The product was extracted with ethyl acetate. The combined organic layers were dried with magnesium sulfate, filtered and concentrated in vacuo. The crude material (0.62 g, 72% yield) was used without further purification in the next step. 1H NMR (400 MHz, CDCl3) δ 7.86-7.83 (m, 2H), 7.73-7.70 (m, 2H), 3.77 (t, J=6.4 Hz, 2H), 3.36 (t, J=8.0 Hz, 2H), 1.94 (m, 2H).

Workup

  1. additionThe tube containing the resulting mixture
  2. customcap
  3. customfitted with a silicon septum
  4. customirradiation for 30 min at a temperature of 120° C
  5. customAfter the irradiation
  6. temperaturethe reaction tube was cooled with high-pressure air until the temperature
  7. customhad fallen below 40° C
  8. extractionThe product was extracted with ethyl acetate
  9. dry with materialThe combined organic layers were dried with magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b17251be6f7489183e0560cd538da2a
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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