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【结 构 式】 
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【分子编号】11039 【品名】2-[tert-Butyl(dimethyl)silyl]-5-(2,3-dimethylbenzoyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide 【CA登记号】 |
【 分 子 式 】C20H31N3O3SSi 【 分 子 量 】421.63606 【元素组成】C 56.97% H 7.41% N 9.97% O 11.38% S 7.61% Si 6.66% |
合成路线1
该中间体在本合成路线中的序号：(IV)A new synthesis for medetomidine has been reported: The silylation of N,N-dimethylimidazole-1-sulfonamide (I) with tert-butyldimethylsilyl chloride and butyllithium in THF gives the 2-silyl derivative (II), which is acylated with 2,3-dimethylbenzoyl chloride (III) by means of butyllithium in THF, yielding 2-(tert-butyldimethylsilyl)-5-(2,3-dimethylbenzoyl)-N,N-dimethylimidazo le-1-sulfonamide (IV). Hydrolysis of (IV) with refluxing aqueous HCl affords 5-(2,3-dimethylbenzoyl)imidazole (V), which is finally methylated with methyllithium in THF and reduced with Li in liquid NH3.
| 【1】 Turnbull, S.P.; Kudzma, L.V.; Expedient synthesis of 4(5)-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole, the alpha2-adrenergic agonist medetomidine. Synthesis 1991, 11, 1201. |
| 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) | 11036 | N,N-Dimethyl-1H-imidazole-1-sulfonamide | 78162-58-0 | C5H9N3O2S | 详情 | 详情 |
| (II) | 11037 | 2-[tert-Butyl(dimethyl)silyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide | C11H23N3O2SSi | 详情 | 详情 | |
| (III) | 11038 | 2,3-Dimethylbenzoyl chloride | 21900-46-9 | C9H9ClO | 详情 | 详情 |
| (IV) | 11039 | 2-[tert-Butyl(dimethyl)silyl]-5-(2,3-dimethylbenzoyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide | C20H31N3O3SSi | 详情 | 详情 | |
| (V) | 11040 | (2,3-Dimethylphenyl)(1H-imidazol-4-yl)methanone | C12H12N2O | 详情 | 详情 |