Sodium Azide → Methyl[1-(3-azidopropyl)cyclopropyl]acetate

HRID 238167Notes

Reaction equation

HRID 238167 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1([CH2:8][CH2:9][CH2:10]Br)[CH2:7][CH2:6]1.[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1([CH2:8][CH2:9][CH2:10][N:13]=[N+:14]=[N-:15])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 58074516Methyl[1-(3-bromopropyl)cyclopropyl]acetate

Product 1

HCID 58074492Methyl[1-(3-azidopropyl)cyclopropyl]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

680 mg (2.89 mmol) of methyl[1-(3-bromopropyl)cyclopropyl]acetate and 1128 mg (17.35 mmol) of sodium azide in 5 ml of DMF were stirred at 60° C. for 2 h. The reaction mixture was then concentrated under reduced pressure. The residue was taken up in ethyl acetate and the solution was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure gave 389 mg (1.97 mmol, 68% of theory) of the title compound as a yellow oil.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. washthe solution was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-78b37aa043e64a5cb1534183f5ad0406
Source dataset
uspto-grants-2014_02
Patent number
US08642592B2

Reaction notes

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