Sodium Azide → 4-(2-Azidoethoxy)benzaldehyde

HRID 2362817Notes

Reaction equation

HRID 2362817 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=2)(=O)=O)=CC=1.[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C=O)C>[N:23]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=1)=[N+:24]=[N-:25]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 37755262-(4-Formylphenoxy)ethyl 4-methylbenzenesulfonate

Product 1

HCID 179225524-(2-Azidoethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5.0 g (15.61 mmol) of the compound from Example 35A and 2.03 g (31.22 mmol) of sodium azide in 100 ml of dry DMF is stirred at RT for 12 h. The reaction mixture is concentrated using a rotary evaporator, and the residue is suspended in about 20 ml of water. After three extractions with in each case 30 ml of diethyl ether, the combined organic phases are washed twice with in each case 10 ml of water and once with 10 ml of saturated sodium chloride solution. After drying over sodium sulphate, the solvent is removed on a rotary evaporator.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customa rotary evaporator
  3. extractionAfter three extractions with in each case 30 ml of diethyl ether
  4. washthe combined organic phases are washed twice with in each case 10 ml of water and once with 10 ml of saturated sodium chloride solution
  5. dry with materialAfter drying over sodium sulphate
  6. customthe solvent is removed on a rotary evaporator

Sources & evidence

ORD record
ord-cf136ad2a50a4b0d98b6a5fdae7a35fd
Source dataset
uspto-grants-2014_04
Patent number
US08691850B2

Reaction notes

Loading…