Sodium Azide → HCID 18334250, compound

HRID 2269419Notes

Reaction equation

HRID 2269419 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13](Br)[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)=[CH:9][CH:8]=1>CN(C)C=O>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([N:1]=[N+:2]=[N-:3])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 18334107HCID 18334107, compound

Product 1

HCID 18334250HCID 18334250, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (26.1 g) was added to a solution of α-(4-methoxyphenyl)-3-nitrobenzyl bromide (25.8 g) in dimethylformamide (200 ml) in an ice bath. The mixture was stirred on the ice bath for 1 hour and then at ambient temperature for 1 hour. The dimethylformamidle was then removed by evaporation under reduced pressure. The residue was partitioned between ethyl acetate and water two times. The ethyl acetate layers were combined and washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column using a 6:1 by volume mixture of hexane and ethyl acetate as the eluant, to afford the title compound (18.6 g) as a yellow oil.

Workup

  1. customThe dimethylformamidle was then removed by evaporation under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water two times
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue was purified by chromatography through a silica gel column
  7. additionby volume mixture of hexane and ethyl acetate as the eluant

Sources & evidence

ORD record
ord-4746d5ae8d0a4da499a3adba8d0faed3
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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