5-Fluoro-2-(4'-amino-3'-iodophenyl)benzothiazole → 2-Amino-5-(5-fluorobenzo[d]thiazol-2-yl)benzonitrile
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([NH2:16])=[C:12](I)[CH:11]=3)=[N:7][C:6]=2[CH:18]=1.[Cu](C#N)[C:20]#[N:21]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([C:20]#[N:21])[CH:11]=3)=[N:7][C:6]=2[CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Fluoro-2-(4′-amino-3′-iodophenyl)benzothiazole (5 g, 0.0135 mol), copper cyanide (3.65 g, 0.04 mol) and DMF (100 ml) were heated under reflux for 6 hrs, cooled and the solvent removed under vacuum. The residue was stirred in water (50 ml) for 30 mins, then the product extracted with ethyl acetate (2×100 ml). The combined extracts were dried (Na2SO4), evaporated and the residue recrystallised from ethanol to give a white solid.