Sodium Azide → 4-(1H-1,2,3,4-tetrazol-5-yl)benzaldehyde

HRID 1068899Notes

Reaction equation

HRID 1068899 reaction equation
[Cl-].[Li+].[N-:3]=[N+:4]=[N-:5].[Na+].[C:7]([C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1)#[N:8]>COC(O)C>[NH:3]1[C:7]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)=[N:8][N:5]=[N:4]1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 660424-CyanobenzaldehydeHCID 433294Lithium Chloride

Product 1

HCID 27606064-(1H-1,2,3,4-tetrazol-5-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Procedure

20.0 g (0.47 mol) of lithium chloride and 20.5 g (0.315 mol) of sodium azide are added to 41.2 9 (0.315 mol) of 4-cyano-benzaldehyde in 310 ml of methoxy-ethanol and the mixture is heated at boiling for 6 hours (argon atmosphere). When cool the reaction mixture is poured into 1 liter of ice/HCl 37% (10:1) and stirred thoroughly to complete the reaction. Filtration and washing with water yield 4-(tetrazol-5-yl)-benzaldehyde; m.p. 180-182° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureWhen cool the reaction mixture
  3. customthe reaction
  4. filtrationFiltration
  5. washwashing with water

Sources & evidence

ORD record
ord-6b3aee83ebf146969017113b12a160c4
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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