Ethyl Acetate → 4-(1H-1,2,3,4-tetrazol-5-yl)benzaldehyde

HRID 1057397Notes

Reaction equation

HRID 1057397 reaction equation
C[Si]([N:5]=[N+:6]=[N-:7])(C)C.C([Sn](=O)CCCC)CCC.[C:18]([C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1)#[N:19].C(OCC)(=O)C>C1(C)C=CC=CC=1>[NH:5]1[C:18]([C:20]2[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=2)=[N:19][N:7]=[N:6]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 61221Dibutyltin oxideHCID 660424-CyanobenzaldehydeHCID 78378Azidotrimethylsilane

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Trimethylsilyl azide (25 g) and dibutyltin oxide (8.8 g) were added to a solution of 4-cyanobenzaldehyde (13 g) in toluene (200 ml). The reaction was stirred with warming to 50° C. over 1 hr, and then warmed to 96° C. over 30 minutes and maintained at that temperature for 3 hours. The solvent was evaporated in vacuo to afford an orange oil which was purified by column chromatography over silica gel (ethyl acetate). The crude product was dissolved in refluxing toluene and allowed to cool with stirring overnight. The resulting slurry was granulated in an ice-bath for 1 hour, filtered and washed with cold toluene. The filtrate was evaporated in vacuo to afford a solid. The solid was dissolved in refluxing ethyl acetate (250 ml) and concentrated to 60 ml by rotary evaporation. The solution was cooled to room temperature and then granulated in an ice bath. The thick slurry was collected by filtration, washed and dried, with warming, in a vacuum oven to afford the title compound, 12 g.

Workup

  1. temperaturewarmed to 96° C. over 30 minutes
  2. temperaturemaintained at that temperature for 3 hours
  3. customThe solvent was evaporated in vacuo
  4. customto afford an orange oil which
  5. customwas purified by column chromatography over silica gel (ethyl acetate)
  6. dissolutionThe crude product was dissolved
  7. temperaturein refluxing toluene
  8. temperatureto cool
  9. stirringwith stirring overnight
  10. filtrationfiltered
  11. washwashed with cold toluene
  12. customThe filtrate was evaporated in vacuo
  13. customto afford a solid
  14. dissolutionThe solid was dissolved
  15. concentrationconcentrated to 60 ml by rotary evaporation
  16. temperatureThe solution was cooled to room temperature
  17. customgranulated in an ice bath
  18. filtrationThe thick slurry was collected by filtration
  19. washwashed
  20. customdried
  21. temperaturewith warming, in a vacuum oven

Sources & evidence

ORD record
ord-771424467bdf4678844e26a0893d6333
Source dataset
uspto-grants-2003_02
Patent number
US06514975B1

Reaction notes

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