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【结 构 式】 
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【分子编号】64968 【品名】2-{[(4-methylphenyl)sulfonyl]amino}benzoic acid 【CA登记号】 |
【 分 子 式 】C14H13NO4S 【 分 子 量 】291.32756 【元素组成】C 57.72% H 4.5% N 4.81% O 21.97% S 11.01% |
合成路线1
该中间体在本合成路线中的序号：(II)Sulfonylation of anthranilic acid (I) with p-toluenesulfonyl chloride under Schotten-Baumann conditions furnishes N-tosyl anthranilic acid (II). After conversion of acid (II) to the corresponding acid chloride (III), Friedel-Crafts condensation with benzene in the presence of AlCl3 leads to the benzophenone (IV). The N-tosyl group of (IV) is then removed upon heating with concentrated sulfuric acid to provide 2-aminobenzophenone (V). Acylation of amine (V) with 4-(aminosulfonyl)benzoyl chloride (VI) yields amide (VII). This is finally cyclized to the target indole compound under McMurry conditions employing an in situ generated low valent titanium reagent.
| 【1】 Hu, W.; Guo, Z.; Chu, F.; Bai, A.; Yi, X.; Cheng, G.; Li, J.; Synthesis and biological evaluation of substituted 2-sulfonyl-phenyl-3-phenyl-indoles: A new series of selective COX-2 inhibitors. Bioorg Med Chem 2003, 11, 7, 1153. |
| 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) | 11661 | 2-Aminobenzoic acid;Anthranilic acid; o-Aminobenzoic acid | 118-92-3 | C7H7NO2 | 详情 | 详情 |
| (II) | 64968 | 2-{[(4-methylphenyl)sulfonyl]amino}benzoic acid | C14H13NO4S | 详情 | 详情 | |
| (III) | 64969 | 2-{[(4-methylphenyl)sulfonyl]amino}benzoyl chloride | C14H12ClNO3S | 详情 | 详情 | |
| (IV) | 64970 | 4-methyl-N-[2-(phenylcarbonyl)phenyl]benzenesulfonamide | C20H17NO3S | 详情 | 详情 | |
| (V) | 21101 | (2-aminophenyl)(phenyl)methanone; 2-Aminobenzophenone | 2835-77-0 | C13H11NO | 详情 | 详情 |
| (VI) | 64971 | 4-(aminosulfonyl)benzoyl chloride | C7H6ClNO3S | 详情 | 详情 | |
| (VII) | 64972 | 4-(aminosulfonyl)-N-[2-(phenylcarbonyl)phenyl]benzamide | C20H16N2O4S | 详情 | 详情 |