Sodium Azide → Methyl 2-azido-2-methoxyacetate

HRID 1658003Notes

Reaction equation

HRID 1658003 reaction equation
Cl[CH:2]([O:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4].[N-:9]=[N+:10]=[N-:11].[Na+]>C(COC)OC>[N:9]([CH:2]([O:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4])=[N+:10]=[N-:11]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 11018941Methyl 2-chloro-2-methoxy-acetate

Product 1

HCID 20357785Methyl 2-azido-2-methoxyacetateYield 72.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of methyl 2-chloro-2-methoxyacetate (13.86 g., 0.1 mole), powdered sodium azide (8.46 g., 0.13 mole) and dry dimethoxyethane (80ml.) is stirred and heated at reflux for 39 hours. After cooling to room temperature, the mixture is filtered to remove salts which are washed with dry ether. Evaporation of the solvents at aspirator pressure leaves a yellow liquid which is distilled to give methyl 2-azido-2-methoxyacetate (10.5 g.) as a water-white liquid (b.p. 75°-77°C./17 mm.).

Workup

  1. temperatureheated
  2. temperatureat reflux for 39 hours
  3. filtrationthe mixture is filtered
  4. customto remove salts which
  5. washare washed with dry ether
  6. customEvaporation of the solvents at aspirator pressure
  7. customleaves a yellow liquid which
  8. distillationis distilled

Sources & evidence

ORD record
ord-4eede6886068485f9df11ad30c1b9b70
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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