Réaction #1509591

Équation de réaction

sodium azide

N-methyl-5-nitro-isophthalamic acid ethyl ester

NaHCO3

triflic anhydride

→

title compound

Rendement 59.1%

3-(1-Methyl-1H-tetrazol-5-yl)-5-nitro-benzoic acid ethyl ester

Rendement 59.1%

Solvants

dichloroethane

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred overnight
2. 2
   Autrethe organic and aqueous layers were separated
3. 3
   Autrethe organic layer dried
4. 4
   Concentrationconcentrated in vacuum

Mode opératoire

To a 2M solution of N-methyl-5-nitro-isophthalamic acid ethyl ester (10 g) in dichloroethane (200 ml) at −20° C. was added pre-cooled triflic anhydride (10 ml) dropwise. This was stirred for 30 min and then sodium azide (4.6 g) was added. This was allowed to warm to room temperature and stirred overnight. The reaction was neutralised with 5% NaHCO3 (aq) solution and the organic and aqueous layers were separated and the organic layer dried and concentrated in vacuum. Flash chromatography (100:0 to 50:50 gradient cyclohexane:EtOAc) afforded the title compound (6.5 g). Rt=1.52 min (method D).

Source