Abstract
Abstract 2-(1-Chloro-2,2-dimethylpropyl)-1-methyl-1 H -imidazole hydrochloride ( 2a ·HCl) was treated with an excess of N,N -dimethylamine at room temperature to give an abnormal addition product, 4,5-bis( N,N -dimethylamino)-1-methyl-2-(2,2-dimethylpropyl)-2-imidazoline ( 4a ), in 74.2% yield together with a normal S N 2 product, 2-(1- N,N -dimethylamino-2,2-dimethylpropyl)-1-methyl-1 H -imidazole ( 3a ), in 15.0% yield. The former might be evolved from a serial double nucleophilic addition of the secondary amine molecules to the imidazole nucleus, which has been generally considered as an electron-excessive and stable aromatic ring.
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