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

HRID 1447180Notes

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]>>[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

Reactant 2

HCID 12152Benzyl azide

HCID 69336Ethyl cyanoformate

Product 1

HCID 12752368ethyl 1-benzyl-1H-tetrazole-5-carboxylate

Conditions

Temperature: 150 °C

Procedure

An equimolar mixture of benzyl azide and ethyl cyanoformate is heated in a bomb under antogenous pressure at 150° C. for 4 hours. The resulting yellow oil is crystallized from hexane to give the title compound, m.p. 58°-61° C.

Workup

customThe resulting yellow oil is crystallized from hexane

Sources & evidence

ORD record: ord-b77491793d714df6a9a04190242037fa
Source dataset: uspto-grants-1982_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04316037

Reaction notes

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