Sodium Azide → HCID 23036246, compound

HRID 1709682Notes

Reaction equation

HRID 1709682 reaction equation
[Cl:1][C:2]([C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([C:14]([Cl:18])=[C:15]([Cl:17])[Cl:16])[CH:13]=1)[CH2:9]Br)=[C:3]([Cl:5])[Cl:4].[N-:19]=[N+:20]=[N-:21].[Na+]>C(O)C>[Cl:1][C:2]([C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([C:14]([Cl:18])=[C:15]([Cl:17])[Cl:16])[CH:13]=1)[CH2:9][N:19]=[N+:20]=[N-:21])=[C:3]([Cl:5])[Cl:4]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 23036220HCID 23036220, compound

Product 1

HCID 23036246HCID 23036246, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of crude 3,5-di(trichlorovinyl)benzyl bromide (7.9 g) and sodium azide (1.9 g) in 200 ml of ethanol was heated at reflux for 1.5 hours. The reaction mixture was concentrated and the residue partitioned between 100 ml of ether and 100 ml of water. The layers were separated and the aqueous Phase further extracted with ether. The ethereal layers were washed with water, dried with MgSO4, and concentrated to give 7.03 g of an oil. This material was chromatographed on silica gel (hexane then 90:10 hexane:CH2Cl2 to give 3.52 g of pure azide.

Workup

  1. temperatureat reflux for 1.5 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue partitioned between 100 ml of ether and 100 ml of water
  4. customThe layers were separated
  5. extractionthe aqueous Phase further extracted with ether
  6. washThe ethereal layers were washed with water
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-52e931f2ad88479888d04c47f90a5d7f
Source dataset
uspto-grants-1990_08
Patent number
US04950673

Reaction notes

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