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【结 构 式】 
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【分子编号】42214 【品名】N-[4-(2-ethyl-1-hydroxybutyl)phenyl]acetamide 【CA登记号】 |
【 分 子 式 】C14H21NO2 【 分 子 量 】235.32628 【元素组成】C 71.46% H 8.99% N 5.95% O 13.6% |
合成路线1
该中间体在本合成路线中的序号：(III)Addition of Grignard reagent (II) to N-(4-formylphenyl)acetamide (I) produced carbinol (III). After conversion of (III) to mesylate (IV), displacement with 1,2,4-triazole (V) afforded triazolyl derivative (VI). Acid hydrolysis of the acetamido group of (VI) furnished aniline (VII). Treatment of aniline (VII) with carbon disulfide and NaOH, followed by methylation with iodomethane, gave the bis(methylthio)methylene derivative (VIII). Alternatively, aniline (VII) was converted to isothiocyanate (IX) by reaction with thiophosgene. The title benzothiazole was finally obtained by condensation of 2-aminobenzenethiol (X) with either (VIII) or (IX).
| 【1】 Venet, M.G.; Mabire, D.J.-P.; Lacrampe, J.F.A.; Sanz, G.C. (Janssen Pharmaceutica NV); N-[4-(heteroarylmethyl)phenyl]-heteroarylamines. EP 0907650; JP 2000503670; US 6124330; WO 9749704 . |
| 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) | 42212 | N-(4-formylphenyl)acetamide | 122-85-0 | C9H9NO2 | 详情 | 详情 |
| (II) | 42213 | bromo(1-ethylpropyl)magnesium | C5H11BrMg | 详情 | 详情 | |
| (III) | 42214 | N-[4-(2-ethyl-1-hydroxybutyl)phenyl]acetamide | C14H21NO2 | 详情 | 详情 | |
| (IV) | 42215 | 1-[4-(acetamido)phenyl]-2-ethylbutyl methanesulfonate | C15H23NO4S | 详情 | 详情 | |
| (V) | 13135 | 1H-1,2,4-Triazole; 1,2,4-Triazole | 288-88-0 | C2H3N3 | 详情 | 详情 |
| (VI) | 42216 | N-[4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl]acetamide | C16H22N4O | 详情 | 详情 | |
| (VII) | 42217 | 4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]aniline; 4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenylamine | C14H20N4 | 详情 | 详情 | |
| (VIII) | 42218 | 1-[1-(4-[[bis(methylsulfanyl)methylene]amino]phenyl)-2-ethylbutyl]-1H-1,2,4-triazole | C17H24N4S2 | 详情 | 详情 | |
| (IX) | 42219 | 1-[2-ethyl-1-(4-isothiocyanatophenyl)butyl]-1H-1,2,4-triazole; 4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl isothiocyanate | C15H18N4S | 详情 | 详情 | |
| (X) | 25182 | 2-aminobenzenethiol | 137-07-5 | C6H7NS | 详情 | 详情 |