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

HRID 1458466Notes

Reaction equation

HRID 1458466 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 g (0.315 mol) of 4-cyano-benzaldehyde (Fluka, Buchs, Switzerland) in 310 ml of methoxyethanol (Fluka, Buchs, Switzerland) and the mixture is heated at boiling for 6 hours (argon atmosphere). The cooled reaction mixture is poured into 1 litre of ice/37% HCl 10:1 and stirred thoroughly to complete the reaction. Filtration and washing with water yield the title compound: m.p.: 180°-182° C.; 1H-NMR (DMSO-d6) δ 10.11 (s, HCO), 8.29 and 8.14 (2d, J=8, each 2H).

Workup

  1. temperaturethe mixture is heated
  2. customThe cooled reaction mixture
  3. customthe reaction
  4. filtrationFiltration
  5. washwashing with water

Sources & evidence

ORD record
ord-5e2520fa6a824d49991de588d8f30ef2
Source dataset
uspto-grants-1998_12
Patent number
US05849911

Reaction notes

Loading…