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【结 构 式】 
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【分子编号】40139 【品名】4-chloro-N,N-dimethylbenzamide 【CA登记号】14062-80-7 |
【 分 子 式 】C9H10ClNO 【 分 子 量 】183.63724 【元素组成】C 58.87% H 5.49% Cl 19.31% N 7.63% O 8.71% |
合成路线1
该中间体在本合成路线中的序号：(A)The hydrolysis of ethyl 1,4-dimethyl-3-ethoxycarbonylpyrrole-2-acetate (I) with refluxing aqueous NaOH gives 3-carboxy-1,4-dimethylpyrrole-2-acetic acid (II), which is partially esterified with refluxing ethanol - dry HCl yielding ethyl 3-carboxy-1,4-dimethylpyrrole-2-acetate (III). The decarboxylation of (III) by heating at 190-210 C affords ethyl 1,4-dimethylpyrrole-2-acetate (IV), which by a Vilsmeier aroylation with p-chloro-N,N-dimethylbenzamide (A) and POCl3 in refluxing dichloroethane is converted into ethyl 5-p-chlorobenzoyl-1,4-dimethylpyrrole-2-acetate (V). Finally, this product is hydrolyzed with refluxing aqueous 1N NaOH.
| 【1】 Hillier, K.; Castañer, J.; Zomepirac. Drugs Fut 1977, 2, 10, 698. |
| 【2】 Wong, S.; Carson, J.R.; 5-Benzoyl-1-methylpyrrole-2-acetic acids as antiinflammatory agents. 2. The 4-methyl compounds. J Med Chem 1973, 16, 2, 172-174. |
| 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) | 40139 | 4-chloro-N,N-dimethylbenzamide | 14062-80-7 | C9H10ClNO | 详情 | 详情 |
| (I) | 40135 | ethyl 2-(2-ethoxy-2-oxoethyl)-1,4-dimethyl-1H-pyrrole-3-carboxylate | C13H19NO4 | 详情 | 详情 | |
| (II) | 40136 | 2-(carboxymethyl)-1,4-dimethyl-1H-pyrrole-3-carboxylic acid | 33369-45-8 | C9H11NO4 | 详情 | 详情 |
| (III) | 40137 | 2-(2-ethoxy-2-oxoethyl)-1,4-dimethyl-1H-pyrrole-3-carboxylic acid | C11H15NO4 | 详情 | 详情 | |
| (IV) | 40138 | ethyl 2-(1,4-dimethyl-1H-pyrrol-2-yl)acetate | C10H15NO2 | 详情 | 详情 | |
| (V) | 40140 | ethyl 2-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]acetate | C17H18ClNO3 | 详情 | 详情 |