N-Iodosuccinimide → (5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-(4-methoxyphenyl)amine
Reaction equation
[S:1]1[C:5]([NH:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[N:4][N:3]2[CH:15]=[CH:16][N:17]=[C:2]12.[I:18]N1C(=O)CCC1=O>CN(C)C=O>[I:18][C:15]1[N:3]2[C:2]([S:1][C:5]([NH:6][C:7]3[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=3)=[N:4]2)=[N:17][CH:16]=1Participants
4
Procedure
Imidazo[2,1-b][1,3,4]thiadiazol-2-yl-(4-methoxyphenyl)amine (0.455 g, 1.85 mmol) was dissolved in N,N-dimethylformamide (8 mL) and N-iodosuccinimide (2.03 mmol, 0.48 g) was added in one portion. The reaction mixture was stirred at room temperature for 22 hours in the absence of light. Solvent was evaporated and the residue was purified by column chromatography (Biotage™/Flash, silica, ethylacetate:dichloromethane 2:8 to 0:10) to give 0.11 g of (5-iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-(4-methoxyphenyl)amine as an off-white solid (16% yield).