反応 #643086

反応方程式

2-Amino-4-chlorobenzonitrile

sodium azide

triethylamine hydrochloride

→

5-Chloro-2-(1H-tetrazol-5-yl)aniline

収率 85.0%

溶媒

toluene

反応条件

後処理

1. 1
   温度After cooling
2. 2
   洗浄the reaction mixture was washed 3 times with 5 mL portions of water
3. 3
   その他The desired 5-Chloro-2-(1H-tetrazol-5-yl)aniline precipitated from aqueous solution
4. 4
   その他was isolated by filtration (1090 mg, 85% yield)

実験手順

2-Amino-4-chlorobenzonitrile (1000 mg, 6.6 mmol), sodium azide (555 mg, 8.5 mmol) and triethylamine hydrochloride (1175 mg, 8.5 mmol) were taken up in 15 mL of toluene. The suspension was heated to 100° C. overnight. After cooling, the reaction mixture was washed 3 times with 5 mL portions of water. The combined aqueous fractions were acidified with concentrated hydrochloric acid. The desired 5-Chloro-2-(1H-tetrazol-5-yl)aniline precipitated from aqueous solution and was isolated by filtration (1090 mg, 85% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.73 (d, 1H), 6.97 (d, 1H), 6.74 (dd, 1H); MS (electrospray) m/z 196 (M+H).

出典