Sodium Iodide → cis-3-Azido-4-oxo-2-azetidinylmethyl iodide

HRID 1112343Notes

Reaction equation

HRID 1112343 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][C@H:6]1[C@@H:9]([N:10]=[N+:11]=[N-:12])[C:8](=[O:13])[NH:7]1)(=O)=O.[Na+].[I-:22]>CC(C)=O>[N:10]([C@H:9]1[C:8](=[O:13])[NH:7][C@H:6]1[CH2:5][I:22])=[N+:11]=[N-:12]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86734335HCID 86734335, compound

Product 1

HCID 86736077cis-3-Azido-4-oxo-2-azetidinylmethyl iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A degassed solution of cis-3-azido-4-oxo-2-azetidinylmethyl tosylate (2.36 g) in acetone (80 ml) was refluxed with NaI (5.85 g) overnight. Reaction was cooled and the acetone was removed in vacuo. The reaction mixture was partitioned between ethyl acetate and aqueous sodium thiosulfate solution. Phases were separated and the organic layer was extracted with thiosulfate solution. The combined aqueous extracts were extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried and evaporated to give an off-white solid. The product was recrystallized from ethyl acetate-hexane, melting point 130°-2° (dec.), 1.5 g (75%).

Workup

  1. customReaction
  2. temperaturewas cooled
  3. customthe acetone was removed in vacuo
  4. customThe reaction mixture was partitioned between ethyl acetate and aqueous sodium thiosulfate solution
  5. customPhases were separated
  6. extractionthe organic layer was extracted with thiosulfate solution
  7. extractionThe combined aqueous extracts were extracted with ethyl acetate
  8. washThe combined ethyl acetate layers were washed with brine
  9. customdried
  10. customevaporated
  11. customto give an off-white solid
  12. customThe product was recrystallized from ethyl acetate-hexane, melting point 130°-2° (dec.), 1.5 g (75%)

Sources & evidence

ORD record
ord-1816e72e44dc498fadd6fba1a9ab65bc
Source dataset
uspto-grants-1978_10
Patent number
US04122086

Reaction notes

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