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【结 构 式】 
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【分子编号】14936 【品名】2-(chloromethyl)-N-isobutyl-N-methylaniline; N-[2-(chloromethyl)phenyl]-N-isobutyl-N-methylamine 【CA登记号】 |
【 分 子 式 】C12H18ClN 【 分 子 量 】211.73436 【元素组成】C 68.07% H 8.57% Cl 16.74% N 6.62% |
合成路线1
该中间体在本合成路线中的序号：(VI)The acylation of methylanthranilate (I) with isobutyryl chloride (II) gives 2-isobutyramidobenzoic acid methyl ester (III), which is reduced with LiAlH4 to 2-(isobutylamino)benzyl alcohol (IV). The methylation of (IV) with dimethyl sulfate yields 2-(N-isobutyl-N-methylamino)benzyl alcohol (V), which is treated with SOCl2 to afford the corresponding benzyl chloride (VI). The condensation of (VI) with benzimidazole-2-thiol (VII) by means of NaOH yields 2-[2-(N-isobutyl-N-methylamino)benzylsulfanyl)benzimidazole (VIII), which is finally oxidized with m-chloroperbenzoic acid (MCPBA) as usual.
| 【1】 Mealy, N.; Castaner, J.; Leminoprazole. Drugs Fut 1996, 21, 2, 155. |
| 【2】 Mazaki, M.; Yamakawa, T.; Nomura, Y. (Nippon Chemiphar Co., Ltd.); Method for the preparation of benzimidazole cpds. JP 1990078665 . |
| 【3】 Okabe, S.; Sato, M.; Yamakawa, T.; Nomura, T.; Hayashi, M. (Nippon Chemiphar Co., Ltd.); Cytoprotective agents for stomach and intestine. JP 1988230633 . |
| 【4】 Susumu, O.; Masaru, S.; Tomio, Y.; Yutaka, N.; Masatoshi, H. (Nippon Chemiphar Co., Ltd.); Benzimidazole derivs. and antiulcer agents contain. AU 8546409; BE 0903128; CH 665417; DE 3531487; ES 8703142; FR 2569691; GB 2163747; JP 1986060660; JP 1986221175; JP 1986221176; JP 1991223260; JP 1991223261; JP 1991223262; JP 1991227927 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 11161 | methyl 2-aminobenzoate; Methyl anthranilate | 134-20-3 | C8H9NO2 | 详情 | 详情 |
| (II) | 14932 | isobutyryl chloride; 2-methylpropanoyl chloride | 79-30-1 | C4H7ClO | 详情 | 详情 |
| (III) | 14933 | methyl 2-(isobutyrylamino)benzoate | C12H15NO3 | 详情 | 详情 | |
| (IV) | 14934 | [2-(isobutylamino)phenyl]methanol | C11H17NO | 详情 | 详情 | |
| (V) | 14935 | [2-[isobutyl(methyl)amino]phenyl]methanol | C12H19NO | 详情 | 详情 | |
| (VI) | 14936 | 2-(chloromethyl)-N-isobutyl-N-methylaniline; N-[2-(chloromethyl)phenyl]-N-isobutyl-N-methylamine | C12H18ClN | 详情 | 详情 | |
| (VII) | 12821 | 2-Mercaptobenzinidiazole; 1H-Benzimidazol-2-ylhydrosulfide; 1H-Benzimidazole-2-thiol; 2-Benzimidazolethiol; o-Phenylenethiourea; 2-Benzimidazolinethione; 1,3-Dihydro-2H-benzimidazole-2-thione | 583-39-1 | C7H6N2S | 详情 | 详情 |
| (VIII) | 14938 | 2-[(1H-benzimidazol-2-ylsulfanyl)methyl]-N-isobutyl-N-methylaniline; N-[2-[(1H-benzimidazol-2-ylsulfanyl)methyl]phenyl]-N-isobutyl-N-methylamine | C19H23N3S | 详情 | 详情 |