Sodium Azide → 4-(2-Azidoacetyl)benzonitrile

HRID 244586

Reaction equation

HRID 244586 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=[O:4].[N-:13]=[N+:14]=[N-:15].[Na+]>CO>[N:13]([CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=[O:4])=[N+:14]=[N-:15]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 986544-(Bromoacetyl)benzonitrile

Product 1

HCID 586617294-(2-Azidoacetyl)benzonitrileYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the commercially available 4-bromoacetyl-benzonitrile (5 g, 22.32 mmol) in 150 mL of methanol was added sodium azide (1.74 g, 26.78 mmol) and the contents stirred at room temperature for 2 h. After removal of the solvent, the residue was treated with water (50 mL) and extracted with dichloromethane (3×50 mL). The combined organic layers were dried over MgSO4 and concentrated to give a yellow solid (3.90 g, 94%). This compound was used for the next step without any further purification.

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was treated with water (50 mL)
  3. extractionextracted with dichloromethane (3×50 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b2c5886bde8446999e9f1ed768a4f001
Source dataset
uspto-grants-2014_02
Patent number
US08658659B2

Linked notes

Loading…