Reaction #1726718

Reaction equation

benzyl 2-benzyloxy-5-cyanobenzoate

sodium azide

ammonium chloride

→

benzyl 2-benzyloxy-5-(1H-tetrazol-5-yl)benzoate

Yield 101.9%

Solvents

DMF

Conditions

Workup

1. 1
   OtherThe DMF was removed by rotoevaporation
2. 2
   FiltrationThe white precipitate is collected by filtration
3. 3
   Otherdried

Procedure

A solution of 436 mg (1.27 mmol) of benzyl 2-benzyloxy-5-cyanobenzoate, 91 mg (1.40 mmol) of sodium azide, and 68 mg (1.27 mmol) of ammonium chloride in 5 mL of DMF is heated at 120° C. for 24 hrs. The DMF was removed by rotoevaporation, the residue is taken up in water, and acidified. The white precipitate is collected by filtration and dried to give 500 mg of unpurified benzyl 2-benzyloxy-5-(1H-tetrazol-5-yl)benzoate, which is treated with 28% aqueous ammonium hydroxide in 5 mL of MeOH at 85° C. for 72 hrs. The reaction mixture was concentrated, taken up in water, and then acidified. Filtration of the precipitate gives 400 mg (1.04 mmol, 82% yield) of 2-benzyloxy-5-(1H-tetrazol-5-yl)benzamide.

Source