Imidazole → HCID 19045277, compound
Reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([OH:12])=[C:7]([C:9](=[O:11])[CH3:10])[CH:8]=1.CN(C)C=O.[Na].[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1>>[C:9]([C:7]1[CH:8]=[C:3]([CH2:2][N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)[CH:4]=[CH:5][C:6]=1[OH:12])(=[O:11])[CH3:10]Participants
4
Procedure
To a mixture of 5'-(chloromethyl)-2'-hydroxyacetophenone (1.85 g, 10.0 mmol), sodium dimethylformamide was added imidazole (0.75 g, 11.0 mmol). The mixture was stirred four hours and concentrated in vacuo. The residue was stirred under 50 mL ethanol, filtered, and the filtrate concentrated in vacuo to give a residue. The residue was stirred under 30 mL chloroform, filtered, and the filtrate concentrated in vacuo to give crude product. The crude product was purified by flash chromatography eluting with 5:95 methanol:chloroform to give a solid. The solid was recrystallized from n-butlychloride to give 0.71 g (33%) product as a yellow crystalline solid, mp 106°-107° C.