Sodium Azide → 5-(3'-Fluoro-4'-methyl-biphenyl-2-yl)-1H-tetrazole

HRID 234759Notes

Reaction equation

HRID 234759 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[CH3:8].[N-:17]=[N+:18]=[N-:19].[Na+].[Cl-].C([NH+](CC)CC)C>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]2[NH:19][N:18]=[N:17][N:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 12698378Triethylazanium chlorideHCID 542386242-(3-Fluoro-4-methylphenyl)benzonitrile

Product 1

HCID 1784237105-(3'-Fluoro-4'-methyl-biphenyl-2-yl)-1H-tetrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.26 g (10.7 mmol) of the compound from Example IV are boiled under reflux with 3.48 g (53.6 mmol) of sodium azide and 7.37 g (53.6 mmol) of triethylammonium chloride in 30 ml of analytical grade dimethylformamide for 24 hours. After cooling, the mixture is partitioned between ether and 1M sulphuric acid, the organic phase is washed with water and dried over sodium sulphate and the solvent is evaporated off. The crude product is extracted by stirring in toluene and, after filtration with suction, the product is dried in vacuo (1.89 g, 7.2 mmol). The mother liquor is evaporated on a rotary evaporator and the residue is purified again as above (0.43 g, 1.7 mmol).

Workup

  1. temperatureAfter cooling
  2. customthe mixture is partitioned between ether and 1M sulphuric acid
  3. washthe organic phase is washed with water
  4. dry with materialdried over sodium sulphate
  5. customthe solvent is evaporated off
  6. extractionThe crude product is extracted
  7. filtrationafter filtration with suction
  8. customthe product is dried in vacuo (1.89 g, 7.2 mmol)
  9. customThe mother liquor is evaporated on a rotary evaporator
  10. customthe residue is purified again as above (0.43 g, 1.7 mmol)

Sources & evidence

ORD record
ord-dcfc921ac1024df7b0ea499b0da0b6ae
Source dataset
uspto-grants-1997_01
Patent number
US05596006

Reaction notes

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