3-Bromobenzonitrile → HCID 178419385、化合物

反応式

[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[Cl-].[NH4+].[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:14][N:13]=[N:12][N:6]=2)[CH:7]=[CH:8][CH:9]=1

参加物

反応条件

温度: 100 °C

実験手順

3-Bromo-benzonitrile 8a (18.2 g, 0.1 mol) and ammonium chloride (5.9 g, 0.11 mol) were dissolved in 80 mL of N,N′-dimethylformamide followed by addition of sodium azide (7.16 g, 0.11 mol) under argon atmosphere. The reaction mixture was heated to 100° C. and reacted overnight. Then the mixture was cooled to 60° C. and concentrated under reduced pressure to remove N,N′-dimethylformamide. The residue was diluted with 100 mL of water and 4 mL of concentrated hydrochloric acid and stirred for 1 hour. The mixture was filtered and dried to obtain the title compound 5-(3-bromo-phenyl)-1H-tetrazole 8b (23 g) as a white solid.