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

HRID 1671588Notes

Reaction equation

HRID 1671588 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-5604f4aff2654f28829600ace1bf8fec
Source dataset
uspto-grants-2011_08
Patent number
US07994325B2

Reaction notes

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