Sodium Azide → 1-(2-Azidoethyl)-2-nitrobenzene

HRID 1664752Notes

Reaction equation

HRID 1664752 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15]>O.C(#N)C>[N:1]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 123638782-Nitrophenethyl bromide

Product 1

HCID 184442461-(2-Azidoethyl)-2-nitrobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Sodium azide (22.8, 0.351 mol) in water (60 mL) was added to a solution of 2-(2-bromoethyl)-nitrobenzene (27.9 g, 0.121 mol) in acetonitrile (120 mL). The reaction was refluxed for 4 h, cooled, and partitioned between methylene chloride and water. The organic phase was washed with saturated brine, and dried over magnesium sulfate. The title compound was obtained as an oil (22.8 g).

Workup

  1. temperatureThe reaction was refluxed for 4 h
  2. temperaturecooled
  3. custompartitioned between methylene chloride and water
  4. washThe organic phase was washed with saturated brine
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-40946e9c09364bc4803ca4e80ef6da30
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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