Ethyl cyanoformate → ethyl 1-(4-methoxybenzyl)-1H-tetrazole-5-carboxylate

HRID 325740Notes

Reaction equation

HRID 325740 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([CH2:7][N:8]=[N+:9]=[N-:10])=[CH:5][CH:4]=1.[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:14]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:14][N:10]=[N:9]2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 69336Ethyl cyanoformateHCID 109317671-(Azidomethyl)-4-methoxybenzene

Product 1

HCID 11097352ethyl 1-(4-methoxybenzyl)-1H-tetrazole-5-carboxylateYield 95.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of crude 4-methoxybenzyl azide (45.3 g; prepared as described below) and ethyl cyanoformate (33 g) in xylene (300 ml) was heated at reflux for 48 hours. The mixture was evaporated at below 40° C. and under reduced pressure to leave a residue of ethyl 1-(4-methoxybenzyl)-1H-tetrazole-5-carboxylate (69.36 g), m.p. 52° C.

Workup

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

Sources & evidence

ORD record
ord-37265387fae74eff98b258c00dbba15b
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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