反应 #1135815

反应方程式

hydrochloric acid

sodium azide

aluminum chloride

sodium nitrite

1-ethoxy-3-isocyanato-2-methylbenzene

→

1-(2-methyl-3-ethoxyphenyl)-1,4-dihydrotetrazole-5-one

溶剂

N,N-dimethylformamide

water

反应条件

后处理

1. 1
   workup.STIRRINGwere stirred for five hours
2. 2
   温度The mixtures were cooled and under ice-
3. 3
   温度cooling, to the reaction mixtures
4. 4
   萃取The mixtures were extracted with ethyl acetate
5. 5
   洗涤the organic layers were washed with water and saturated saline
6. 6
   干燥were dried over anhydrous magnesium sulfate
7. 7
   浓缩were then concentrated under reduced pressure

实验过程

Under ice-cooling, to a mixture of N,N-dimethylformamide 350 mL and anhydrous aluminum chloride 33.6 g was added sodium azide 15 g, and the resulting mixtures were stirred for one hour. Thereto was thereafter added 1-ethoxy-3-isocyanato-2-methylbenzene described in Reference Preparation example 2737.2 g and the resulting mixtures were heated to 75° C. and were stirred for five hours. The mixtures were cooled and under ice-cooling, to the reaction mixtures was added ice water 100 mL, followed by addition of a mixture of sodium nitrite 23 g and water 150 mL, and the mixtures were acidified with concentrated hydrochloric acid to pH about 4. The mixtures were extracted with ethyl acetate and the organic layers were washed with water and saturated saline, and were dried over anhydrous magnesium sulfate and were then concentrated under reduced pressure. The resulting residues were subjected to a silica gel column chromatography to give 1-(2-methyl-3-ethoxyphenyl)-1,4-dihydrotetrazole-5-one 39.0 g.

来源