Sodium Azide → 5-Azidopentanoic acid ethyl ester

HRID 386421Notes

Reaction equation

HRID 386421 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C)C=O.O>[N:11]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N+:12]=[N-:13]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 84580Ethyl 5-bromovalerate

Product 1

HCID 123821765-Azidopentanoic acid ethyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl 5-bromovalerate (2.1 g; 10 mmol; Aldrich) was added to a stirred suspension of sodium azide (1.3 g, 20 mmol; Fisher) in 5 ml dimethylformamide and 5 ml water, and the reaction mixture was heated 12 h at 80° Cs. The reaction was partitioned between diethyl ether (100 ml) and water (100 ml), and the resulting organic layer was washed with water (100 ml) and brine (100 ml), dried over sodium sulfate, and dried in vacuo. Yield: 1.6 g (9.3 mmol, 95% yield).

Workup

  1. temperaturethe reaction mixture was heated 12 h at 80° Cs
  2. customThe reaction was partitioned between diethyl ether (100 ml) and water (100 ml)
  3. washthe resulting organic layer was washed with water (100 ml) and brine (100 ml)
  4. dry with materialdried over sodium sulfate
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ebf09f29840241ea95cb9dc7b6c8384b
Source dataset
uspto-grants-2013_02
Patent number
US08372839B2

Reaction notes

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