On February 10, 2009, Wan, Huan; Fang, Feng; Duan, Mei-Li; Xu, Xu; Ji, Ya-Fei published an article.Reference of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole The title of the article was Synthesis of 6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole (omeprazole). And the article contained the following:
A method for the synthesis of the title compound [i.e., 6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole, omeprazole] is reported here. Omeprazole is a proton pump inhibitor. A one-pot method was performed for the oxidation and nitration of of 2,3,5-trimethylpyridine to provide 2,3,5-dimethylpyridine N-oxide. The chlorination of that intermediate gave 2-(chloromethyl)-3,5-dimethyl-4-nitropyridine 1-oxide. A reaction of this chloromethyl compound with 2-mercapto-5-methoxybenzimidazole in the presence of excess sodium methoxide simultaneously achieved a condensation and methoxylation to give 6-methoxy-2-[[(4-methoxy-3,5-dimethyl-1-oxido-2-pyridinyl)methyl]thio]-1H-benzimidazole. The target compound was formed by deoxidation with phosphorus trichloride and the oxidation with sodium perborate in an overall yield of 48.7%. The structures of the intermediates and omeprazole were confirmed by 1H NMR and MS. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Reference of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole
The Article related to omeprazole preparation, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Reference of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem