Sodium Azide → Tert-butyl (2-(2-azidoethoxy)ethyl)carbamate

HRID 1920268Notes

Reaction equation

HRID 1920268 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=O)=O>CN(C)C=O.O>[N:1]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 12106196tert-butyl N-{2-[2-(methanesulfonyloxy)ethoxy]ethyl}carbamate

Product 1

HCID 12106197Tert-butyl (2-(2-azidoethoxy)ethyl)carbamateYield 95.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Sodium azide (16.8 g, 259 mmol) was added to a solution of 2-{2-[(tert-butoxycarbonyl)amino]ethoxy}ethyl methanesulfonate (66.9 g, 236 mmol) in N,N-dimethylformamide (400 mL). The reaction was heated at 90° C. for 1.5 hours. The reaction mixture was allowed to cool to ambient temperature, diluted with cold water (500 mL) and then extracted with diethyl ether (4×300 mL). The combined extracts were washed with water (4×100 mL) and brine (1×200 mL), dried over magnesium sulfate and then concentrated under reduced pressure to provide 52 g of tert-butyl 2-(2-azidoethoxy)ethylcarbamate.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with diethyl ether (4×300 mL)
  3. washThe combined extracts were washed with water (4×100 mL) and brine (1×200 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c782cca8868481a989c8f86f44ac11a
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Reaction notes

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