Acetonitrile → 1-(2-Azidoethyl)-2-nitrobenzene

HRID 459883Notes

Reaction equation

HRID 459883 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:7])=[O:6].[C:14](#N)[CH3:15]>O>[N:1]([CH2:14][CH2:15][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N+:5]([O-:7])=[O:6])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 7416NitrobenzeneHCID 33557Sodium Azide

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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-ca3ffbfb48e143118905178ecbc49ba1
Source dataset
uspto-grants-2007_03
Patent number
US07196079B2

Reaction notes

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