3-[(4-nitrophenoxy)methyl]benzonitrile -Drug Synthesis Database

【结构式】

【分子编号】34216

【品名】3-[(4-nitrophenoxy)methyl]benzonitrile

【CA登记号】

【分子式】C₁₄H₁₀N₂O₃

【分子量】254.24508

【元素组成】C 66.14% H 3.96% N 11.02% O 18.88%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IX)

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.

参考文献中间体

合成目标

【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

Extended Information