2-Nitrobenzyl chloride → 1-(Azidomethyl)-2-nitrobenzene

HRID 2412824Notes

Reaction equation

HRID 2412824 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Cl)([O-:3])=[O:2].[N-:12]=[N+:13]=[N-:14].[Na+]>C(O)C>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][N:12]=[N+:13]=[N-:14])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 119212-Nitrobenzyl chlorideHCID 33557Sodium Azide

Product 1

HCID 134517441-(Azidomethyl)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Nitrobenzylchloride dissolved in ethanol is heated at reflux with a 10% molar excess of sodium azide for from six to eight hours. Insoluble salts are removed by filtration, the ethanol removed, and the resultant oil is dissolved in diethyl ether. Additional insoluble material is removed by filtration and 2-nitrobenzylazide is obtained as a pale yellow oil by removal of the diethyl ether.

Workup

  1. temperatureis heated
  2. customInsoluble salts are removed by filtration
  3. customthe ethanol removed
  4. dissolutionthe resultant oil is dissolved in diethyl ether
  5. customAdditional insoluble material is removed by filtration

Sources & evidence

ORD record
ord-7e6a8568d5e14bacb2b029a88e0ef1de
Source dataset
uspto-grants-1985_01
Patent number
US04495101

Reaction notes

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