Benzyl azide → ethyl 1-benzyl-1H-tetrazole-5-carboxylate

HRID 325739Notes

Reaction equation

HRID 325739 reaction equation
[CH2:1]([N:8]=[N+:9]=[N-:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:12]>C1(C)C(C)=CC=CC=1>[CH2:1]([N:8]1[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:12][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12152Benzyl azideHCID 69336Ethyl cyanoformate

Product 1

HCID 12752368ethyl 1-benzyl-1H-tetrazole-5-carboxylateYield 93.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of freshly prepared benzyl azide (1.3 g) and ethyl cyanoformate (1.0 g) in xylene (10 ml) was heated at reflux for 48 hours. The mixture was evaporated under reduced pressure and below 40° C. to give a residue of ethyl 1-benzyl-1H-tetrazole-5-carboxylate (2.13 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours
  3. customThe mixture was evaporated under reduced pressure and below 40° C.

Sources & evidence

ORD record
ord-471225cacb9649ef93dc189a337bd6f4
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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