Reaktion #1509591

Reaktionsgleichung

sodium azide

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

NaHCO3

triflic anhydride

→

title compound

Ausbeute 59.1%

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

Ausbeute 59.1%

Lösungsmittel

dichloroethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle