Cyanogen Bromide → 4-[(5-Amino-1,3,4-oxadiazol-2-yl)methyl]phenol

反応式

Br[C:2]#[N:3].[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([NH:14][NH2:15])=[O:13])=[CH:7][CH:6]=1>CO.O>[NH2:3][C:2]1[O:13][C:12]([CH2:11][C:8]2[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=2)=[N:14][N:15]=1

参加物

反応条件

温度: 2.5 °C

実験手順

Solid BrCN 6.059 g (57.2 mmol) was added in one portion into ice-cooled slurry of (4-hydroxy-phenyl)-acetic acid hydrazide 8.642 g (52.0 mmol) and KHCO3 6.510 g (65 mmol) in MeOH (100 mL). The mixture was stirred at 0-5° C. for 1 hour, the ice bath allowed to melt and stirred at room temperature overnight (18 hr). The reaction mixture was diluted with water (100 mL), stirred for 1 hour, the precipitate was collected by filtration, washed with water and dried on high vacuum. A second fraction precipitated after concentrating and cooling the supernatants.