반응 #643086

반응 방정식

2-Amino-4-chlorobenzonitrile

sodium azide

triethylamine hydrochloride

→

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

수율 85.0%

용매

toluene

반응 조건

후처리

1. 1
   온도After cooling
2. 2
   세척the reaction mixture was washed 3 times with 5 mL portions of water
3. 3
   기타The desired 5-Chloro-2-(1H-tetrazol-5-yl)aniline precipitated from aqueous solution
4. 4
   기타was isolated by filtration (1090 mg, 85% yield)

실험 절차

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).

출처