Sodium Azide → (4-Azidobut-1-ynyl)triethylsilane

HRID 1777559Notes

Reaction equation

HRID 1777559 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CC1C=CC(S(O[CH2:16][CH2:17][C:18]#[C:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])(=O)=O)=CC=1>CN(C=O)C>[N:1]([CH2:16][CH2:17][C:18]#[C:19][Si:20]([CH2:25][CH3:26])([CH2:21][CH3:22])[CH2:23][CH3:24])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 120301384-(Triethylsilyl)but-3-yn-1-yl 4-methylbenzene-1-sulfonate

Product 1

HCID 86663839(4-Azidobut-1-ynyl)triethylsilaneYield 103.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium azide (1.80 g; 27.65 mmol) was added to a solution of 4-(triethylsilyl)but-3-ynyl 4-methylbenzenesulfonate (3.12 g; 9.22 mmol) in DMF (15 mL) and stirred at 60° C. for 3 hours. After cooling, the volatiles were removed under reduced pressure and the residue was partitioned between saturated ammonium chloride and ethyl acetate. The organic layer was dried and concentrated under reduced pressure to afford 2.0 g (quantitative yield) of the desired compound as a colorless oil.

Workup

  1. temperatureAfter cooling
  2. customthe volatiles were removed under reduced pressure
  3. customthe residue was partitioned between saturated ammonium chloride and ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a127a6e1dfe43e2ab455f8dd65f5b28
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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