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【结 构 式】 
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【分子编号】34176 【品名】4-[(1-methylcyclohexyl)methoxy]benzenediazonium chloride 【CA登记号】 |
【 分 子 式 】C14H19ClN2O 【 分 子 量 】266.77044 【元素组成】C 63.03% H 7.18% Cl 13.29% N 10.5% O 6% |
合成路线1
该中间体在本合成路线中的序号：(V)The reaction of 1-methylcyclohexylmethanol (II) with 4-chloronitrobenzene (III) by means of NaH in hot DMSO gives 4-(1-methylcyclohexylmethoxylnitrobenzene (III), which is reduced with H2 over Pd/C in methanol yielding 4-(1-methylcyclohexylmethoxylaniline (IV). Diazotation of (IV) with NaNO2 and HCl in water affords a solution of the corresponding diazonium chloride (V), which is condensed with methyl acrylate (VI) by means of Cu2O affording methyl 2-chloro-3-[4-(1-methylcyclohexylmethoxyl)phenyl]propionate (VII). The cyclization of (VII) with thiourea (VIII) by means of sodium acetate in hot 2-methoxyethanol gives 2-imino-5-[4-(1-methylcyclohexylmethoxy)benzyl]thiazolidin-4-one (IX), which is finally hydrolyzed with HCl in refluxing 2-methoxyethanol - water.
| 【1】 Kawamatsu, Y.; Mizuno, K.; Sugiyama, Y.; Imamiya, E.; Fujita, T.; Sohda, T.; Studies on antidiabetic agents. II. Synthesis of 5-[4-(1-methylcyclohexylmethoxy)benzyl]thiazolidine-2,4-dione (ADD-3878) and its derivatives. Chem Pharm Bull 1982, 30, 10, 3580. |
| 【2】 Nohria, V.; Castaner, J.; Serradell, M.N.; Ciglitazone. Drugs Fut 1984, 9, 4, 258. |
| 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) | 34173 | (1-methylcyclohexyl)methanol | C8H16O | 详情 | 详情 | |
| (II) | 13909 | 1-Chloro-4-nitrobenzene; p-Nitrochlorobenzene | 100-00-5 | C6H4ClNO2 | 详情 | 详情 |
| (III) | 34174 | 1-[(1-methylcyclohexyl)methoxy]-4-nitrobenzene; (1-methylcyclohexyl)methyl 4-nitrophenyl ether | C14H19NO3 | 详情 | 详情 | |
| (IV) | 34175 | 4-[(1-methylcyclohexyl)methoxy]phenylamine; 4-[(1-methylcyclohexyl)methoxy]aniline | C14H21NO | 详情 | 详情 | |
| (V) | 34176 | 4-[(1-methylcyclohexyl)methoxy]benzenediazonium chloride | C14H19ClN2O | 详情 | 详情 | |
| (VI) | 14156 | methyl acrylate | 96-33-3 | C4H6O2 | 详情 | 详情 |
| (VII) | 34177 | methyl 2-chloro-3-[4-[(1-methylcyclohexyl)methoxy]phenyl]propanoate | C18H25ClO3 | 详情 | 详情 | |
| (VIII) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (IX) | 34178 | 2-imino-5-[4-[(1-methylcyclohexyl)methoxy]benzyl]-1,3-thiazolidin-4-one | C18H24N2O2S | 详情 | 详情 |