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【结 构 式】 
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【分子编号】34218 【品名】3-([4-[(2,3-dihydroxypropyl)amino]phenoxy]methyl)benzonitrile 【CA登记号】 |
【 分 子 式 】C17H18N2O3 【 分 子 量 】298.3416 【元素组成】C 68.44% H 6.08% N 9.39% O 16.09% |
合成路线1
该中间体在本合成路线中的序号：(XII)A shorter synthetic pathway is through the condensation of the above chlorohydrin (II) with m-cyanobenzyloxyaniline (X), prepared by alkylation of p-nitrophenol (VIII) with m-cyanobenzyl bromide (VII) in the presence of KI and further reduction of the nitro group with Fe-NH4Cl, then cyclization with ethyl carbonate. Cimoxatone can also be obtained by opening glycidol (XI) with m-cyanobenzyloxyaniline (X) in ethanol under reflux, and cyclizing with ethyl carbonate (A) to obtain a 5-hydroxymethyl-2-oxazolidinone (XIII), which is methylated by CH3I under phase-transfer catalysis.
| 【1】 Ancher, J.F.; Bourgery, G.; Dostert, P.; Douzon, C.; Guerret, P.; Lacour, A.; Laglois, M.; Nouvelles oxazolidinones, oxazolidinethiones et pyrrilidinones, leur procédé de préparation et leur application en thérapeutique. FR 2428032; JP 55051064; JP 56167666 . |
| 【2】 Ancher, J.F.; Cimoxatone. Drugs Fut 1984, 9, 6, 412. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 17470 | diethyl carbonate; diethylcarbonate | 105-58-8 | C5H10O3 | 详情 | 详情 |
| (II) | 34214 | 1-chloro-3-methoxy-2-propanol | 4151-97-7 | C4H9ClO2 | 详情 | 详情 |
| (VII) | 13244 | alpha-Bromo-m-tolunitrile; 3-(Bromomethyl)benzonitrile | 28188-41-2 | C8H6BrN | 详情 | 详情 |
| (VIII) | 11236 | 4-Nitrophenol; p-Nitrophenol | 100-02-7 | C6H5NO3 | 详情 | 详情 |
| (IX) | 34216 | 3-[(4-nitrophenoxy)methyl]benzonitrile | C14H10N2O3 | 详情 | 详情 | |
| (X) | 34217 | 3-[(4-aminophenoxy)methyl]benzonitrile | C14H12N2O | 详情 | 详情 | |
| (XI) | 29648 | 2-oxiranylmethanol | 556-52-5 | C3H6O2 | 详情 | 详情 |
| (XII) | 34218 | 3-([4-[(2,3-dihydroxypropyl)amino]phenoxy]methyl)benzonitrile | C17H18N2O3 | 详情 | 详情 | |
| (XIII) | 34219 | 3-([4-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenoxy]methyl)benzonitrile | C18H16N2O4 | 详情 | 详情 | |
| (XIV) | 34220 | 3-([4-[(2-hydroxy-3-methoxypropyl)amino]phenoxy]methyl)benzonitrile | C18H20N2O3 | 详情 | 详情 |