反応 #1509591

反応方程式

sodium azide

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

NaHCO3

triflic anhydride

→

title compound

収率 59.1%

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

収率 59.1%

溶媒

dichloroethane

反応条件

後処理

1. 1
   workup.STIRRINGstirred overnight
2. 2
   その他the organic and aqueous layers were separated
3. 3
   その他the organic layer dried
4. 4
   濃縮concentrated in vacuum

実験手順

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).

出典