Réaction #1997

Équation de réaction

hydrochloric acid

N,N-dimethylformamide

benzonitrile

sodium azide

→

product

Rendement 90.1%

5-Phenyltetrazole

Rendement 90.1%

Solvants

water

Conditions de réaction

Traitement

1. 1
   Températurewhile maintaining the temperature below 60° C
2. 2
   TempératureThe heterogeneous mixture was heated at 115° C. with agitation for 18 hours
3. 3
   TempératureThe mixture was cooled to room temperature
4. 4
   TempératureThe mixture was cooled to 0° C. and aged for one hour
5. 5
   Filtrationfiltered
6. 6
   Lavagethe filter cake washed with 15 mL of cold 0.1N HCl
7. 7
   Autrethen dried at 60° C. under vacuum

Mode opératoire

Zinc chloride (3.3 g, 24.3 mmol, 0.5 eq) was added to 15 mL of N,N-dimethylformamide in small portions while maintaining the temperature below 60° C. The suspension of zinc chloride was cooled to room temperature and treated with 5.0 g of benzonitrile (48.5 mmol, 1.0 eq) followed by 3.2 g of sodium azide (48.5 mmol, 1.0 eq). The heterogeneous mixture was heated at 115° C. with agitation for 18 hours. The mixture was cooled to room temperature, water (30 mL) was added and the mixture acidified by the addition of 5.1 mL of concentrated hydrochloric acid. The mixture was cooled to 0° C. and aged for one hour, then filtered and the filter cake washed with 15 mL of cold 0.1N HCl then dried at 60° C. under vacuum to afford 6.38 g (43.7 mmol, 90%) of the product.

Source