Cl.Cl[CH2:3][C:4]1[N:5]([CH2:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[CH:11]=2)[CH:6]=[CH:7][N:8]=1.[C:18]1([CH:25]=[CH:24][CH:23]=[C:21]([OH:22])[CH:20]=1)[OH:19].C([O-])([O-])=O.[K+].[K+].Cl>O.CS(C)=O>[Cl:17][C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([Cl:16])[CH:13]=1)[CH2:9][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[CH2:3][O:19][C:18]1[CH:20]=[C:21]([OH:22])[CH:23]=[CH:24][CH:25]=1
To a mixture of 2-chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride (156 mg, 0.5 mmol), resorcinol (330 mg, 3.0 mmol) and DMSO (1 mL) was added K2CO3 (691 mg, 5.0 mmol). The reaction was stirred at ambient temperature for 14 h before diluting with water (20 mL). A solution of 1N HCl was added until the mixture was made only slightly basic (pH 8) before extracting with EtOAc (30 mL). The EtOAc phase was washed with water (10 mL), dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 1:2 to 1:3 hexane/EtOAc then 100% EtOAc) to provide the title compound (113 mg, 65%) as an off-white solid: ESI MS m/z 349 [C17H14Cl2N2O2+H]+.
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