[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[S:10][C:9](N)=[N:8][N:7]=1.[BrH:12].N([O-])=O.[Na+]>O>[Br:12][C:9]1[S:10][C:6]([CH:2]2[CH2:3][CH2:4][CH2:5][O:1]2)=[N:7][N:8]=1To 5-(Tetrahydro-furan-2-yl)-[1,3,4]thiadiazol-2-ylamine (0.5 g, 2.9 mmol) was added 48% HBr (7 ml) and H2O (7 ml). The reaction mixture was cooled to 0° C. using an icebath. Cu(I)Br (0.42 g, 2.9 mmol) was added, followed by a the dropwise addition of solution of NaNO2 (0.48 g, 10 mmol) in H2O (18 ml). The reaction mixture was stirred for a further 10 mins at 0° C. then allowed to warm up to room temperature over a 35 min period. A solution of saturated bicarbonated was added to the reaction mixture until the pH=6, then extracted with EtOAc, dried (MgSO4), filtered and the solvent removed in vacuo to afford the product (0.5 g, 2.1 mmol). MS: [M+H]+235, 237.
Loading…
