Reaction #5040

Reaction equation

HCl

nitrile

4-benzyloxybenzonitrile

triethylamine hydrochloride

sodium azide

→

5-(4-benzyloxyphenyl)tetrazole

Yield 98.1%

Solvents

water

DMF

Conditions

Workup

1. 1
   Temperatureunder reflux for 18 hrs
2. 2
   OtherThe resulting white solid was collected
3. 3
   Washwashed with water
4. 4
   Otherdried at 60° C. in vacuo for 48 hrs

Procedure

A mixture of 285 g of the nitrile, 262.5 g triethylamine hydrochloride and 124 g of sodium azide in 1.5 L of DMF under nitrogen was stirred under reflux for 18 hrs. The reaction mixture was cooled to room temperature, poured into 4 L of cold water and acidified with 3N HCl. The resulting white solid was collected, washed with water and dried at 60° C. in vacuo for 48 hrs to give 337 g of 5-(4-benzyloxyphenyl)tetrazole.

Source