Sodium Azide → 2-Azido-1-(4-nitrophenyl)ethanone

HRID 28596

Reaction equation

HRID 28596 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:4].[N-:14]=[N+:15]=[N-:16].[Na+]>O1CCCC1.C(O)C.O>[N:14]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:4])=[N+:15]=[N-:16]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 668402-Bromo-4'-nitroacetophenone

Product 1

HCID 167492572-Azido-1-(4-nitrophenyl)ethanone

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-bromo-1-(4-nitro-phenyl)-ethanone (2.0 g, 8.2 mmol) in tetrahydrofuran (15 ml) and ethanol (15 ml) was added a solution of sodium azide (586 mg, 9.8 mmol) in water (1.5 ml). After stirring for 20 minutes, the mixture was concentrated under reduced pressure. The residue was treated with saturated aqueous sodium chloride solution (200 ml) and extracted with ethyl acetate (200 ml). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give crude 2-azido-1-(4-nitrophenyl)-ethanone.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionThe residue was treated with saturated aqueous sodium chloride solution (200 ml)
  3. extractionextracted with ethyl acetate (200 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5782194270b84c77a8c805d693f2ce3c
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

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