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【结 构 式】 
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【药物名称】Moracizine hydrochloride, Moricizine hydrochloride, E-350, E-313, Ethmozine 【化学名称】10-(3-Morpholinopropionyl)phenothiazine-2-carbamic acid ethyl ester hydrochloride 【CA登记号】31883-05-3 (free base) 【 分 子 式 】C22H26ClN3O4S 【 分 子 量 】463.98722 |
【开发单位】Bristol-Myers Squibb (Originator) 【药理作用】Antiarrhythmic Drugs, CARDIOVASCULAR DRUGS |
合成路线1
The reaction of 3-aminodiphenylamine (I) with ethyl chloroformate (A) gives ethyl 3-anilinocarbanilate (II), which is cyclized by heating with S and I2 to yield ethyl phenothiazine-2-carbamate (III). The condensation of (III) with 3-chloropropionyl chloride (B) in refluxing toluene affords ethyl 10-(3-chloropropionyl)phenothiazine-2-carbamate (IV), which is finally condensed with refluxing morpholine (C).
| 【1】 Gritsenko, A.N.; et al.; Synthesis of ethmosine [hydrochloride of the ethyl ester of 10-(beta-morpholylpropionyl)phenothiazine-2-carbamic acid], a new antiarrhytmic preparation. Khim Farm Zh 1972, 6, 9, 17-19. |
| 【2】 Gritsenko, A.N.; et al.; Antiarhythmic pharmaceutical preparation containing ethyl 10-(beta-morpholylpropionyl) phenthiazine-2-carbamate hydrochloride. DE 2014201; US 3864487 . |
| 【3】 Gritsenko, A.N.; et al.; Ethyl 10-(beta-N-morpholinylpropionyl)phenthiazine-2-carbamate and the hydrochloride thereof and a method for preparing the same. GB 1269969 . |
| 【4】 Gritsenko, A.N.; et al.; Ethyl 10-(beta-morpholinylpropionyl)phenthiazine-2-carbamate hydrochloride. US 3740395 . |
| 【5】 Castaner, J.; Roberts, P.J.; Moracizine. Drugs Fut 1978, 3, 2, 122. |
| 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) | 11229 | 1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate | 541-41-3 | C3H5ClO2 | 详情 | 详情 |
| (B) | 18936 | 3-chloropropanoyl chloride | 625-36-5 | C3H4Cl2O | 详情 | 详情 |
| (I) | 33468 | N(1)-phenyl-1,3-benzenediamine; N-(3-aminophenyl)-N-phenylamine | C12H12N2 | 详情 | 详情 | |
| (II) | 33469 | ethyl 3-anilinophenylcarbamate; Diphenylamino-3-carbaminoethyl ester | 86517-37-6 | C15H16N2O2 | 详情 | 详情 |
| (III) | 33470 | ethyl 10H-phenothiazin-2-ylcarbamate; Phenothiazine-2-ethylcarbamate | 37711-29-8 | C15H14N2O2S | 详情 | 详情 |
| (IV) | 11351 | ethyl N-[10-(3-chloropropanoyl)-10H-phenothiazin-2-yl]carbamate | C18H17ClN2O3S | 详情 | 详情 | |
| (C) | 10388 | Morpholine | 110-91-8 | C4H9NO | 详情 | 详情 |
Extended Information