Imidazole → HCID 59333320, compound
Reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.I[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=1[N+:18]([O-:20])=[O:19]>C(OCC)(=O)C>[N+:18]([C:8]1[CH:9]=[C:10]([O:13][C:14]([F:15])([F:16])[F:17])[CH:11]=[CH:12][C:7]=1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)([O-:20])=[O:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1H-imidazole (818 mg, 12 mmol, 4 eq) and 1-iodo-2-nitro-4-(trifloromethoxy)benzene (1.0 g, 3 mmol, 1 eq) under argon are heated with a heat-gun at between 300 and 500° C. for 45 min until 1-iodo-2-nitro-4-(trifluoromethoxy)benzene has completely reacted on TLC monitoring. The crude mixture is cooled to room temperature, diluted in ethyl acetate and washed with a saturated solution of ammonium chloride. The organic phase is dried over sodium sulfate and concentrated under vacuum. Purification on silica gel (95/05 dichloromethane/methanol) afforded the title compound (570 mg, 2.08 mmol, 69%) as a yellow powder.