Bromine → 9-Bromo-4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH3:19])[S:17][C:13]=2[N:12]2[CH:20]=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1.[Br:23]Br>ClC(Cl)C>[Br:23][C:20]1[N:12]2[C:13]3[S:17][C:16]([CH2:18][CH3:19])=[CH:15][C:14]=3[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[N:9][CH2:10][C:11]2=[N:22][N:21]=1Participants
4
Procedure
4-(2-Chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (10 g) was dissolved in dichloroethane (100 ml), and bromine (1.7 ml) was added under ice-cooling. The mixture was heated to room temperature, and allowed to stand overnight. The solvent was evaporated, and chloroform was added. The mixture was washed with an aqueous sodium thiosulfate solution, a saturated aqueous sodium hydrogencarbonate solution and brine, and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (developing solvent:ethyl acetate-hexane) and crystallized from ethyl acetate to give 3.4 g of 9-bromo-4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine.