Sodium Azide → 2-Azido-1,3-dimethoxypropane

HRID 1760511Notes

Reaction equation

HRID 1760511 reaction equation
[CH3:1][O:2][CH2:3][CH:4](OS(C)(=O)=O)[CH2:5][O:6][CH3:7].[N-:13]=[N+:14]=[N-:15].[Na+]>CC(N(C)C)=O.O>[CH3:1][O:2][CH2:3][CH:4]([N:13]=[N+:14]=[N-:15])[CH2:5][O:6][CH3:7]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 225957861,3-Dimethoxypropan-2-yl methanesulfonate

Product 1

HCID 225957772-Azido-1,3-dimethoxypropaneYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

1,3-Dimethoxy-2-methanesulphonyloxypropane (Method 49; 3.74 g, 19 mmol) and sodium azide (2.03 g, 31 mmol) in DMA (55 ml) was heated at 100° C. for 8 hours then left to stand at ambient temperature for 24 hours. The mixture was diluted with water, extracted with ethyl acetate, the extracts combined and washed with water, dried (MgSO4) and the volatiles removed by evaporation to give the title compound (2.0 g, 74%) as a clear oil.

Workup

  1. waitthen left
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customthe volatiles removed by evaporation

Sources & evidence

ORD record
ord-1ae6644ab41f452b8f9ecec49d33796b
Source dataset
uspto-grants-2005_01
Patent number
US06844341B2

Reaction notes

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