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【结 构 式】 
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【分子编号】59374 【品名】2-benzoyl-N-(2-hydroxyethyl)-N-methylbenzamide 【CA登记号】24833-47-4 |
【 分 子 式 】C17H17NO3 【 分 子 量 】283.32692 【元素组成】C 72.07% H 6.05% N 4.94% O 16.94% |
合成路线1
该中间体在本合成路线中的序号：(V)The reaction of 3-phenylphthalide (I) with N-methylethanolamine (II) in refluxing benzene gives N-(2-hydroxyethyl)-2-(1-hydroxy-1-phenylmethyl)-N-methylbenzamide (III), which is cyclized by means of Ts-OH in refluxing toluene to yield 5-methyl-1-phenyl-3,4,5,6-tetrahydro-1H-2,5-benzoxazocin-6-one (IV). Finally this compound is reduced with LiAlH4 in refluxing THF to afford the target benzoxazocine. In an alternative method, the reduction of 2-benzoyl-N-(2-hydroxyethyl)-N-methylbenzamide (V) by means of sodium bis(2-methoxyethoxy)aluminum hydride in refluxing toluene gives the diol (VI), which is then cyclized by means of Ts-OH in refluxing toluene, or by means of aq. 48% HBr in hot chloroform to afford the target benzoxazocine.
| 【1】 Lucero de Pablo, M.L.; Martin-Escudero Perez, U.; Izquierdo Sanjose, M.; Process for the preparation of a benzoxazine deriv. and its non-toxic salt. ES 8105723 . |
| 【2】 Eberlin, J.W.; Process for benz[f]-2,5-oxazocines. US 3978085 . |
| 【3】 Gimbert Roura, J.; Soler Peix, E.; Process for the preparation of benzoxazines. KE 8201564 . |
| 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) | 59371 | 3-Phenyl-1(3H)-isobenzofuranone; 3-Phenylphthalide | 5398-11-8 | C14H10O2 | 详情 | 详情 |
| (II) | 13324 | 2-Methylaminoethanol; 2-(Methylamino)-1-ethanol | 109-83-1 | C3H9NO | 详情 | 详情 |
| (III) | 59372 | N-(2-hydroxyethyl)-2-[hydroxy(phenyl)methyl]-N-methylbenzamide | C17H19NO3 | 详情 | 详情 | |
| (IV) | 59373 | 5-methyl-1-phenyl-4,5-dihydro-1H-2,5-benzoxazocin-6(3H)-one | C17H17NO2 | 详情 | 详情 | |
| (V) | 59374 | 2-benzoyl-N-(2-hydroxyethyl)-N-methylbenzamide | 24833-47-4 | C17H17NO3 | 详情 | 详情 |
| (VI) | 59375 | 2-[{2-[hydroxy(phenyl)methyl]benzyl}(methyl)amino]-1-ethanol | C17H21NO2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)The reaction of 2-benzoylbenzoic acid (I) with PCl3 in dichloromethane gives the corresponding acyl chloride (II), which is condensed with N-methylethanolamine (III) by means of TEA In dichloroethane to yield the amide (IV). The reaction of (IV) with PCl3 in dichloroethane affords the 2-chloroethylamide (V), which is reduced with NaBH4 and A-OH in dichloromethane to provide the diol (VI). Finally, this compound is cyclized by means of aq. HBr in dichloroethane to give the target benzoxazocine.
| 【1】 Watson, P.G.; Process for the preparation of 2-[N-(2-hydroxyethyl)-N-lower alkylaminomethyl]benzhydrols. US 4208349 . |
| 【2】 Watson, P.G.; Process for the preparation of 2-[N-(2-hydroxyethyl)-N-lower alkylaminomethyl)benzhydrols. GB 1586578 . |
| 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) | 59365 | 2-benzophenone carboxylic acid; 2-Benzoylbenzoic acid; 2-Carboxybenzophenone; Benzophenone-2-carboxylic acid; O-benzoylbenzoic acid | 85-52-9 | C14H10O3 | 详情 | 详情 |
| (II) | 59366 | 2-benzoylbenzoyl chloride | C14H9ClO2 | 详情 | 详情 | |
| (III) | 13324 | 2-Methylaminoethanol; 2-(Methylamino)-1-ethanol | 109-83-1 | C3H9NO | 详情 | 详情 |
| (IV) | 59374 | 2-benzoyl-N-(2-hydroxyethyl)-N-methylbenzamide | 24833-47-4 | C17H17NO3 | 详情 | 详情 |
| (V) | 59377 | 2-benzoyl-N-(2-chloroethyl)-N-methylbenzamide | C17H16ClNO2 | 详情 | 详情 | |
| (VI) | 59375 | 2-[{2-[hydroxy(phenyl)methyl]benzyl}(methyl)amino]-1-ethanol | C17H21NO2 | 详情 | 详情 |