Sodium Azide → HCID 19703033, compound

HRID 1777520Notes

Reaction equation

HRID 1777520 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C:14]#[C:15][Si:16]([CH3:19])([CH3:18])[CH3:17])(=O)=O)=CC=1.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C=O)C>[N:20]([CH2:12][CH2:13][C:14]#[C:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[N+:21]=[N-:22]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 13197283HCID 13197283, compound

Product 1

HCID 19703033HCID 19703033, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(trimethylsilyl)but-3-ynyl 4-methylbenzenesulfonate (1.38 g; 4.65 mmol) and sodium azide (0.908 g; 13.96 mmol) in DMF (5 mL) was heated at 60° C. for 2 hours and concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with an aqueous solution of saturated ammonium chloride, dried and concentrated under reduced pressure to yield 0.700 g (90%) of (4-azidobut-1-ynyl)trimethylsilane which was used without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with an aqueous solution of saturated ammonium chloride
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8da3119902384ef78d2db48a6f35d495
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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