Water → 5-Cyano-2-(2,6-dichloro-4-trifluoromethylphenyl)imidazole
Reaction equation
[C:1]([C:3]1[NH:7][C:6]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=2[Cl:19])=[N:5][C:4]=1C(O)=O)#[N:2].O>C(O)COCCO>[C:1]([C:3]1[NH:7][C:6]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:16])([F:18])[F:17])=[CH:10][C:9]=2[Cl:19])=[N:5][CH:4]=1)#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 170 °C
Procedure
A solution of 5-cyano-2-(2,6-dichloro-4-trifluoromethylphenyl)imidazole-4-carboxylic acid (7.09 g, 0.02 mol) in diethyleneglycol (70 ml) was stirred and heated at 170° C. in an atmosphere of nitrogen for 36 hours. The reaction mixture was cooled to room temperature and water (150 ml) was added. The reaction mixture was extracted with ethyl acetate (2×100 ml), washed with water (50 ml), dried over anhydrous sodium sulphate and evaporated to dryness. The solid residue was purified by chromatography on silica gel eluting with a mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.)(1:1) and recrystallised from a mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.) to give 5-cyano-2-(2,6-dichloro-4-trifluoromethylphenyl)imidazole (2.15 g) as a white solid m.p. 210°-212° C.