N-(2,3-Epoxypropyl)phthalimide → N-(3-Azido-2-hydroxypropyl)phthalimide

HRID 1793788Notes

Reaction equation

HRID 1793788 reaction equation
[O:1]1[CH2:15][CH:2]1[CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].[N-:16]=[N+:17]=[N-:18].[Na+].[Cl-].[NH4+]>CN(C=O)C>[N:16]([CH2:15][CH:2]([OH:1])[CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14])=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 21601N-(2,3-Epoxypropyl)phthalimideHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 10857754N-(3-Azido-2-hydroxypropyl)phthalimideYield 92.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To DMF solution (400 ml) of N-(2,3-epoxypropyl)phthalimide 58.8 g (0.29 mol), sodium azide 37.6 g (0.58 mol) and ammonium chloride 18.5 g (0.35 mol) were added, and stirred at 90° C. for 3 hours. The reaction mixture was cooled to room temperature, and then filtered. The filtrate was evaporated to dryness. The residue was dissolved in benzene (800 ml), washed with water, brine and water sequentially and then dried over sodium sulfate. The solvent was removed in vacuo. The desired product was further purified by silica gel chromatography. 66.3 g of desired product was obtained. The NMR spectra were consistent with the desired title intermediate.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated to dryness
  4. dissolutionThe residue was dissolved in benzene (800 ml)
  5. washwashed with water, brine and water sequentially
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed in vacuo
  8. customThe desired product was further purified by silica gel chromatography

Sources & evidence

ORD record
ord-c65962aac3b0466480cb63e291f5cf1e
Source dataset
uspto-grants-2006_04
Patent number
US07022677B1

Reaction notes

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