Reaction #70941

Reaction equation

hydrochloric acid

3,4-bis-benzyloxy-5-nitro-benzonitrile

sodium azide

ammonium chloride

→

5-(3,4-bis-benzyloxy-5-nitro-phenyl)-2H-tetrazole

Solvents

dimethylformamide

Conditions

Workup

1. 1
   TemperatureAfter cooling to room temperature
2. 2
   workup.ADDITIONthe reaction mixture was poured onto water (30 mL)
3. 3
   OtherThe resulting precipitate was collected
4. 4
   Washwashed with water
5. 5
   Otherdried

Procedure

A mixture of 3,4-bis-benzyloxy-5-nitro-benzonitrile (0.54 g, 1.50 mmol), sodium azide (0.15 g, 2.25 mmol) and ammonium chloride (0.12 g, 2.25 mmol) in dimethylformamide (3 mL) was stirred at 85° C. for 20 hours. After cooling to room temperature, the reaction mixture was poured onto water (30 mL) and acidified with dilute hydrochloric acid. The resulting precipitate was collected, washed with water and dried to yield 5-(3,4-bis-benzyloxy-5-nitro-phenyl)-2H-tetrazole, 0.53 g (87%).

Source