Reacción #1509591

Ecuación de reacción

sodium azide

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

NaHCO3

triflic anhydride

→

title compound

Rendimiento 59.1%

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

Rendimiento 59.1%

Disolventes

dichloroethane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente