N-Iodosuccinimide → 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-iodopyrazole
Reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:9][C:8]=2[Cl:19])[N:5]=[C:4]([C:20]#[N:21])[CH:3]=1.[I:22]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([O:14][C:15]([F:17])([F:16])[F:18])=[CH:9][C:8]=2[Cl:19])[N:5]=[C:4]([C:20]#[N:21])[C:3]=1[I:22]Participants
4
Procedure
To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)pyrazole (4.17 g) in acetonitrile (20 ml) at room temperature was added N-iodosuccinimide (2.79 g). After 15 minutes the mixture was evaporated to dryness and the residual orange solid was taken up in dichloromethane. The solution was washed with water, then brine, then dried (Na2SO4) and evaporated to provide the title compound as a pale orange solid, m.p. 149.5-150.0° C.