Sodium Azide → HCID 21956457, compound

HRID 2213726Notes

Reaction equation

HRID 2213726 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:20]#[N:21])=[CH:8][N:9]2[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[CH:4][C:3]=1[N+:23]([O-:25])=[O:24].[N-:26]=[N+:27]=[N-:28].[Na+]>CS(C)=O>[N:26]([C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:20]#[N:21])=[CH:8][N:9]2[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[CH:4][C:3]=1[N+:23]([O-:25])=[O:24])=[N+:27]=[N-:28]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 102711017-Chloro-6-nitro-4-oxo-1-([2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrile

Product 1

HCID 21956457HCID 21956457, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6.0 g (15.8 mmol) of 7-chloro-6-nitro-4-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrile in 120 mL of dimethyl sulfoxide is added 5.13 g (79.0 mmol) of sodium azide and the resulting mixture is stirred at room temperature for 3 hours. The mixture is then heated at 60° C. for 10 minutes, room temperature for 1 hour and then poured on to ice. The solid is collected by filtration, washed thoroughly with water and dried in vacuo to yield 6.1 g of 7-azido-6-nitro-4-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrile as a yellow solid.

Workup

  1. temperatureThe mixture is then heated at 60° C. for 10 minutes, room temperature for 1 hour
  2. additionpoured on to ice
  3. filtrationThe solid is collected by filtration
  4. washwashed thoroughly with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-db8f86b07d644f38a14981c6e5a82bca
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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