Sodium Azide → HCID 23036246, compound

HRID 2414162Notes

Reaction equation

HRID 2414162 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-d071fc46adbe4616b8ec2087e5e3b20f
Source dataset
uspto-grants-1988_01
Patent number
US04721791

Reaction notes

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