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【结 构 式】 
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【分子编号】34186 【品名】N-phenethylacetamide 【CA登记号】877-95-2 |
【 分 子 式 】C10H13NO 【 分 子 量 】163.21936 【元素组成】C 73.59% H 8.03% N 8.58% O 9.8% |
合成路线1
该中间体在本合成路线中的序号：(VII)The condensation of 4-[2-(acetylamino)ethyl]benzenesulfonyl chloride (I) with 1-cyclohexyl-2-iminoimidazolidine (III) by means of NaOH in refluxing acetone gives 1-[[4-(2-acetamidoethyl)phenyl]sulfonyl]-3-cyclohexyl-2-iminoimidazolidine (III), which is hydrolyzed with refluxing 2N HCl yielding 1-[[4-(2-aminoethyl)phenyl]sulfonyl]-3-cyclohexyl-2-iminoimidazolidine (IV). Finally, this compound is acylated with crotonic anhydride (V) in dioxane. The starting products (I) and (II) are obtained as follows: 1) The acetylation of 2-phenylethylamine (VI) with acetic anhydride gives N-(2-phenylethyl)acetamide (VII), which is sulfonated with chlorosulfonic acid yielding compound (I). 2) The reductocondensation of cyclohexanone (IX) with ethylenediamine (VIII) gives N-cyclohexylethylenediamine (X), which is then cyclized with cyanogen chloride to compound (II).
| 【1】 Lehmann, C.; Dietrich, H.; Schweizer, E.H.; Marki, F.; Sulfonyliminoimidazolidines. A new clas of oral hypoglycemic agents. I. 1-[[p-[2-(Acylamino)ethyl]phenyl]sulfonyl]-2-iminoimidazolidies. J Med Chem 1983, 26, 7, 964-970. |
| 【2】 Serradell, M.N.; Castaner, J.; Thorpe, P.J.; CGP-11112. Drugs Fut 1984, 9, 5, 315. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIIII) | 14754 | ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine | 107-15-3 | C2H8N2 | 详情 | 详情 |
| (I) | 34181 | 4-[2-(acetamido)ethyl]benzenesulfonyl chloride | C10H12ClNO3S | 详情 | 详情 | |
| (II) | 34182 | 1-cyclohexyl-2-imidazolidinimine | C9H17N3 | 详情 | 详情 | |
| (III) | 34183 | N-[4-[(3-cyclohexyl-2-imino-1-imidazolidinyl)sulfonyl]phenethyl]acetamide | C19H28N4O3S | 详情 | 详情 | |
| (IV) | 34184 | 2-[4-[(3-cyclohexyl-2-imino-1-imidazolidinyl)sulfonyl]phenyl]-1-ethanamine; 4-[(3-cyclohexyl-2-imino-1-imidazolidinyl)sulfonyl]phenethylamine | C17H26N4O2S | 详情 | 详情 | |
| (V) | 34185 | (E)-2-butenoic anhydride | C8H10O3 | 详情 | 详情 | |
| (VI) | 18333 | Phenethylamine; 2-Phenyl-1-ethanamine | 64-04-0 | C8H11N | 详情 | 详情 |
| (VII) | 34186 | N-phenethylacetamide | 877-95-2 | C10H13NO | 详情 | 详情 |
| (IX) | 11059 | Cyclohexanone | 108-94-1 | C6H10O | 详情 | 详情 |
| (X) | 34187 | N(1)-cyclohexyl-1,2-ethanediamine; N-(2-aminoethyl)-N-cyclohexylamine | C8H18N2 | 详情 | 详情 |