Water → Acetic acid, azido-, ethyl ester

HRID 2185675Notes

Reaction equation

HRID 2185675 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[N-:8]=[N+:9]=[N-:10].[Na+].O>C(#N)C>[N:8]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N+:9]=[N-:10]

Participants

5

Reactant 3

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 33557Sodium Azide

Product 1

HCID 69480Acetic acid, azido-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl bromoacetate (150 g, 0.901 mol) in dry acetonitrile (800 ml) was treated with sodium azide (58.57 g, 0.901 mol) under a nitrogen atmosphere, and the mixture was heated at reflux for 20 hours. After cooling, water (50 ml) was added and the mixture was stirred for half an hour; the upper phase was separated out and the lower phase was treated with a salt and extracted with diethyl ether. The organic phases were combined and the solvent removed at a temperature not exceeding 50° C., in order to give a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 20 hours
  3. temperatureAfter cooling
  4. customthe upper phase was separated out
  5. additionthe lower phase was treated with a salt
  6. extractionextracted with diethyl ether
  7. customthe solvent removed at a temperature not
  8. customexceeding 50° C., in order
  9. customto give a yellow oil

Sources & evidence

ORD record
ord-69b83a00e9b94eb1b13d2adb9c65edcd
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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