Acetone → 2-Azidomethyl-2-hydroxy-1,3-diazidopropane

HRID 2215862

Reaction equation

HRID 2215862 reaction equation
[N:1]([CH2:4][C:5]([CH2:7][N:8]=[N+:9]=[N-:10])=[O:6])=[N+:2]=[N-:3].[N-:11]=[N+:12]=[N-:13].[Na+].[CH3:15]C(C)=O>>[N:1]([CH2:4][C:5]([OH:6])([CH2:15][N:11]=[N+:12]=[N-:13])[CH2:7][N:8]=[N+:9]=[N-:10])=[N+:2]=[N-:3]

Participants

4

Reactant 3

HCID 180AcetoneHCID 33557Sodium AzideHCID 121381971,3-Diazidoacetone

Product 1

HCID 121382042-Azidomethyl-2-hydroxy-1,3-diazidopropane

Procedure

To a solution of 1,3-diazidoacetone 7(10 gms, 0.07 mol) in aq. acetone (20 mL water, 150 mL acetone) was added sodium azide (15 gm, 0.23 mol) and the resulting mixture was heated under reflux for 14 hours. The reaction mixture was concentrated under reduced pressure and partitioned between water and methylene chloride. The organic layer was separated, dried over sodium sulfate and concentrated to obtain a residue that was chromatographed to obtain pure 2-azidomethyl-2-hydroxy-1,3-diazidopropane 2.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 14 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. custompartitioned between water and methylene chloride
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto obtain a residue that
  9. customwas chromatographed

Sources & evidence

ORD record
ord-87366408e5574a2d98d670d245d26388
Source dataset
uspto-grants-2006_09
Patent number
US07109359B1

Linked notes

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