Sodium Azide → (3-Phthalimidoacetonyl)azide

HRID 1730389Notes

Reaction equation

HRID 1730389 reaction equation
[C:1]1(=[O:16])[N:5]([CH2:6][C:7](=[O:10])[CH2:8]Br)[C:4](=[O:11])[C:3]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]12.[N-:17]=[N+:18]=[N-:19].[Na+]>>[C:1]1(=[O:16])[N:5]([CH2:6][C:7](=[O:10])[CH2:8][N:17]=[N+:18]=[N-:19])[C:4](=[O:11])[C:3]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]12

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 2220372-(3-bromo-2-oxopropyl)-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 12707120(3-Phthalimidoacetonyl)azideYield 95%

Procedure

A suspension of (3-phthalimidoacetonyl)bromide, ethylene ketal (70.0 g, 210mmole) and sodium azide (33.0 g, 504 mmole) in 25 ml. of dimethyl sulfoxideis heated on a steambath under nitrogen for 4 days. The above mixture is poured onto ice and extracted with chloroform (3×, 500 ml). The chloroform extract is washed with water (2×), saturated sodium chloride solution and dried over anhydrous sodium sulfate. Evaporation of chloroform in vacuo gives a white oil which on trituration with hexane crystallizes to afford 59 g, (95%) of (3-phthalimidoacetonyl)azide, ethylene ketal as white prisms of melting point 90.5°-92° C.An analytical sample recrystallized from ethyl acetate hexane has a meltingpoint 92.5°-93.5° C.

Workup

  1. temperatureof dimethyl sulfoxideis heated on a steambath under nitrogen for 4 days
  2. additionThe above mixture is poured onto ice
  3. extractionextracted with chloroform (3×, 500 ml)
  4. extractionThe chloroform extract
  5. washis washed with water (2×), saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customEvaporation of chloroform in vacuo
  8. customgives a white oil which on trituration with hexane
  9. customcrystallizes

Sources & evidence

ORD record
ord-bc71f660abbf4948a6939ba46c0d0786
Source dataset
uspto-grants-1976_11
Patent number
US03992408

Reaction notes

Loading…