2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-(2,6-Dichloro-4-trifluoromethylphenyl)-4,5-dicyanoimidazole
反応式
[NH2:1][C:2]([C:20]#[N:21])=[C:3]([N:6]=[CH:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=1[Cl:19])[C:4]#[N:5].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(#N)C>[Cl:14][C:13]1[CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=[C:9]([Cl:19])[C:8]=1[C:7]1[NH:1][C:2]([C:20]#[N:21])=[C:3]([C:4]#[N:5])[N:6]=1参加物
4
実験手順
A solution of 1-amino-2-(2,6-dichloro-4-trifluoromethylbenzylideneamino)-1,2-dicyanoethylene (3.3 g, 0.01 mol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (3.3 g, 0.01 mol) in acetonitrile (75 ml) was stirred at reflux for 48 hours. Evaporation of the solvent yielded a brown solid which was continuously extracted with boiling toluene. The solution was evaporated under reduced pressure and the red-brown residue was dissolved in a mixture of ethyl acetate and dichloromethane (1:10) and filtered through silica. Evaporation of the liltrate gave a brown solid which was triturated with hexane and the solid was removed by filtration to give 2-(2,6-dichloro-4-trifluoromethylphenyl)-4,5-dicyanoimidazole (1.4 g) as a light brown solid, m.p. 194°-195° C.