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【结 构 式】 
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【分子编号】56528 【品名】sodium 2-(aminosulfonyl)benzoate 【CA登记号】 |
【 分 子 式 】C7H6NNaO4S 【 分 子 量 】223.184748 【元素组成】C 37.67% H 2.71% N 6.28% Na 10.3% O 28.67% S 14.37% |
合成路线1
该中间体在本合成路线中的序号：(I)Saccharin (II) was obtained by acidification of a solution of sodium 2-sulfamoylbenzoate (I). Alkylation of the sulfimide N of (II) with N-(2-pyridyl)bromoacetamide (III) under phase-transfer conditions afforded (IV). Rearrangement of sulfimide (IV) in the presence of sodium methoxide gave rise to the benzothiazine derivative (V). From this, the title compound was prepared by two related ways. Esterification of (V) with trimethylacetyl chloride yielded pivalate ester (VI), which was subsequently alkylated at the sulfamide N with iodomethane in the presence of NaOH. Alternatively, methylation of (V), followed by esterification of the resultant (VII) with pivaloyl chloride led to the title compound.
| 【1】 Chiesi, P.; Villani, F. (Chiesi Farmaceutici SpA); Benzo-1,2-thiazine 1,1-dioxide derivs., their preparation and their use. BE 0895712; EP 0085866 . |
| 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) | 56528 | sodium 2-(aminosulfonyl)benzoate | C7H6NNaO4S | 详情 | 详情 | |
| (II) | 11298 | 1H-1,2-Benzisothiazole-1,1,3(2H)-trione; Saccharin | 81-07-2 | C7H5NO3S | 详情 | 详情 |
| (III) | 56529 | 2-bromo-N-(2-pyridinyl)acetamide | C7H7BrN2O | 详情 | 详情 | |
| (IV) | 56530 | N-(2-pyridinyl)-2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)acetamide | C14H11N3O4S | 详情 | 详情 | |
| (V) | 56531 | 4-hydroxy-1,1-dioxo-N-(2-pyridinyl)-1,2-dihydro-1lambda~6~,2-benzothiazine-3-carboxamide | C14H11N3O4S | 详情 | 详情 | |
| (VI) | 56532 | 1,1-dioxo-3-[(2-pyridinylamino)carbonyl]-1,2-dihydro-1lambda~6~,2-benzothiazin-4-yl pivalate | C19H19N3O5S | 详情 | 详情 | |
| (VII) | 56533 | Piroxicam; 4-Hhydroxy-2-methyl-3-[pyrid-2-ylcarbamoyl]-2H-1,2-benzothiazine 1,1-dioxide | 36322-90-4 | C15H13N3O4S | 详情 | 详情 |