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【结 构 式】 
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【分子编号】34884 【品名】6-(trifluoromethoxy)-1,3-benzothiazol-2-ylamine; 6-(trifluoromethoxy)-1,3-benzothiazol-2-amine 【CA登记号】1744-22-5 |
【 分 子 式 】C8H5F3N2OS 【 分 子 量 】234.2017896 【元素组成】C 41.03% H 2.15% F 24.34% N 11.96% O 6.83% S 13.69% |
合成路线1
该中间体在本合成路线中的序号：(II)Treatment of 4-(trifluoromethoxy)aniline (I) with thiocyanogen, generated from KSCN and Br2 in cold AcOH, afforded riluzole (II). Regioselective alkylation of (II) with 2-(methylthio)ethyl chloride (III) in refluxing methyl ethyl ketone then gave the title compound.
| 【1】 Barreau, M.; Audiau, F.; Jimonet, P.; et al.; Riluzole series. Synthesis and in vivo "antiglutamate" activity of 6-substituted-2-benzothiazolamines and 3-substituted-2-imino-benzothiazolines. J Med Chem 1999, 42, 15, 2828. |
| 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) | 11131 | 4-(Trifluoromethoxy)aniline; 4-(Trifluoromethoxy)phenylamine | 461-82-5 | C7H6F3NO | 详情 | 详情 |
| (II) | 34884 | 6-(trifluoromethoxy)-1,3-benzothiazol-2-ylamine; 6-(trifluoromethoxy)-1,3-benzothiazol-2-amine | 1744-22-5 | C8H5F3N2OS | 详情 | 详情 |
| (III) | 16149 | 2-Chloroethyl methyl sulfide; 1-Chloro-2-(methylsulfanyl)ethane | 542-81-4 | C3H7ClS | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)Treatment of 4-(trifluoromethoxy)aniline (I) with thiocyanogen, generated from KSCN and Br2 in cold AcOH, afforded riluzole (II). Regioselective alkylation of (II) with 2-(methylthio)ethyl chloride (III) in refluxing methyl ethyl ketone then gave compound (IV), which was finally oxidized to the title sulfoxide by means of m-chloroperbenzoic acid.
| 【1】 Barreau, M.; Audiau, F.; Jimonet, P.; et al.; Riluzole series. Synthesis and in vivo "antiglutamate" activity of 6-substituted-2-benzothiazolamines and 3-substituted-2-imino-benzothiazolines. J Med Chem 1999, 42, 15, 2828. |
| 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) | 11131 | 4-(Trifluoromethoxy)aniline; 4-(Trifluoromethoxy)phenylamine | 461-82-5 | C7H6F3NO | 详情 | 详情 |
| (II) | 34884 | 6-(trifluoromethoxy)-1,3-benzothiazol-2-ylamine; 6-(trifluoromethoxy)-1,3-benzothiazol-2-amine | 1744-22-5 | C8H5F3N2OS | 详情 | 详情 |
| (III) | 16149 | 2-Chloroethyl methyl sulfide; 1-Chloro-2-(methylsulfanyl)ethane | 542-81-4 | C3H7ClS | 详情 | 详情 |
| (IV) | 34885 | 3-[2-(methylsulfanyl)ethyl]-6-(trifluoromethoxy)-1,3-benzothiazol-2(3H)-imine | C11H11F3N2OS2 | 详情 | 详情 |