Reaction #1997

Reaction equation

hydrochloric acid

N,N-dimethylformamide

benzonitrile

sodium azide

→

product

Yield 90.1%

5-Phenyltetrazole

Yield 90.1%

Solvents

water

Conditions

Workup

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

Procedure

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