反応 #1135792

反応方程式

sodium nitrite

hydrochloric acid

aluminum chloride

sodium azide

1-fluoro-3-isocyanato-2-methylbenzene

→

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

収率 95.1%

溶媒

water

N,N-dimethylformamide

反応条件

後処理

1. 1
   workup.STIRRINGthe resulting mixtures were stirred for fifteen minutes
2. 2
   温度After cooling the mixtures
3. 3
   workup.ADDITIONwas added the reaction solutions
4. 4
   workup.STIRRINGwith stirring
5. 5
   抽出were extracted with ethyl acetate
6. 6
   洗浄The organic layers were washed with water and saturated saline
7. 7
   乾燥were dried over anhydrous magnesium sulfate
8. 8
   濃縮were then concentrated under reduced pressure

実験手順

Under ice-cooling, to N,N-dimethylformamide 250 mL was added anhydrous aluminum chloride 21.9 g and the resulting mixtures were stirred for fifteen minutes. Thereto was added sodium azide 10.7 g and the resulting mixtures were stirred for fifteen minutes and thereto was then added 1-fluoro-3-isocyanato-2-methylbenzene 22.5 g and the resulting mixtures were heated at 80° C. for three and a half hours. After cooling the mixtures, to a mixture of sodium nitrite 34 g, water 2 L and ice 500 g was added the reaction solutions with stirring. The mixtures were acidified with 10% hydrochloric acid and were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, and were dried over anhydrous magnesium sulfate and were then concentrated under reduced pressure to give 1-(2-methyl-3-fluorophenyl)-1,4-dihydrotetrazole-5-one 27.5 g.

出典