Dimethylformamide → 2-(3-Chloro-5-methoxy-phenoxymethyl)-1-(3,5-dichloro-benzyl)-1H-imidazole

Reaction equation

[C:1]([O-:4])([O-])=O.[K+].[K+].[ClH:7].Cl[CH2:9][C:10]1[N:11]([CH2:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)[CH:12]=[CH:13][N:14]=1.CN([CH:27]=[O:28])C>>[Cl:7][C:17]1[CH:18]=[C:27]([CH:20]=[C:21]([O:4][CH3:1])[CH:16]=1)[O:28][CH2:9][C:10]1[N:11]([CH2:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)[CH:12]=[CH:13][N:14]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 68862721chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride

Product 1

HCID 119514242-(3-Chloro-5-methoxy-phenoxymethyl)-1-(3,5-dichloro-benzyl)-1H-imidazoleYield 49%

Procedure

3,-Chloro-5-methoxy-1-phenol was dissolved in anhydrous DMF and K2CO3 was added. The reaction mixture was stirred at room temperature for 15 min and chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride (see Example 1) was added to the reaction mixture. The resulting mixture was stirred at room temperature for 36 h. The mixture was diluted with FtOAc and washed with water (×2). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was then purified by silica gel prep TLC using CH2Cl2:MeOH 98:2 as an eluent to afford the title compound (56 mg, 49%); MS m/z 397 [C18H15Cl3N2O2+H]+.