Azide → HCID 3111494, compound

HRID 254261Notes

Reaction equation

HRID 254261 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].C([Sn]([N:26]=[N+:27]=[N-:28])(CCCC)CCCC)CCC.[N-]=[N+]=[N-]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]1[N:26]=[N:27][NH:28][N:5]=1

Participants

5

Reactant 3

HCID 33558AzideHCID 855042-Chloro-5-nitrobenzonitrileHCID 4984872Tributyltin azide

Product 1

HCID 3111494HCID 3111494, compoundYield 127.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

137 mg (0.750 mmol, 1 eq.) of 2-chloro-5-nitrobenzonitrile are dissolved in 8 mL of toluene, and 411 μl (1.5 mmol, 2 eq.) of tributyl tin azide are added to the reaction mixture. Then the mixture is heated under reflux of the toluene for one night. As the reaction is incomplete, 205 μl (0.75 mmol, 1 eq.) of azide are again added and the mixture is stirred under reflux for a further 5 hours. The mixture is then concentrated and 10 mL of HCl 2 N in Et2O are added, the precipitate formed is filtered and washed with pentane and diethyl ether. 216 mg of product 10 are obtained (yield=64%).

Workup

  1. temperatureThen the mixture is heated
  2. temperatureunder reflux for a further 5 hours
  3. concentrationThe mixture is then concentrated
  4. addition10 mL of HCl 2 N in Et2O are added
  5. customthe precipitate formed
  6. filtrationis filtered
  7. washwashed with pentane and diethyl ether

Sources & evidence

ORD record
ord-2d59dff6797242b098cd552bc8ff72ea
Source dataset
uspto-grants-2011_01
Patent number
US07875609B2

Reaction notes

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