【结 构 式】 |
【分子编号】39114 【品名】N-(5-benzoyl-2-nitrophenyl)acetamide 【CA登记号】 |
【 分 子 式 】C15H12N2O4 【 分 子 量 】284.27136 【元素组成】C 63.38% H 4.25% N 9.85% O 22.51% |
合成路线1
该中间体在本合成路线中的序号:(III)The acetylation of 4-aminobenzophenone (I) with acetic anhydride in hot benzene gives 4-acetamidobenzophenone (II), which is nitrated with 90% HNO3 in acetic acid-acetic anhydride yielding 4-acetamido-3-nitrobenzophenone (III). The hydrolysis of (III) with H2SO4 affords 4-amino-3-nitrobenzophenone (IV), which is reduced with H2 over Raney-Ni in THF to give 3,4-diaminobenzophenone (V). The cyclization of (V) with cyanogen bromide in methanol-water gives rise to 2-amino-5-benzoylbenzimidazol (VI), which is treated with isopropylsulfonyl chloride (A) and NaH in dimethoxyethane affording 2-amino-1-isopropylsulfonyl-6-benzoylbenzimidazol (VII). Finally, this compound is treated with hydroxylamine hydrochloride in refluxing methanol.
【1】 Paget, C.J.; et al.; DE 2638551 . |
【2】 Castaner, J.; Hopkins, S.J.; AR-336. Drugs Fut 1980, 5, 3, 120. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(A) | 18477 | 2-propanesulfonyl chloride | 10147-37-2 | C3H7ClO2S | 详情 | 详情 |
(I) | 39112 | 3-Aminobenzophenone; (3-aminophenyl)(phenyl)methanone | 2835-78-1 | C13H11NO | 详情 | 详情 |
(II) | 39113 | N-(3-benzoylphenyl)acetamide | 58202-86-1 | C15H13NO2 | 详情 | 详情 |
(III) | 39114 | N-(5-benzoyl-2-nitrophenyl)acetamide | C15H12N2O4 | 详情 | 详情 | |
(IV) | 39115 | (3-amino-4-nitrophenyl)(phenyl)methanone | C13H10N2O3 | 详情 | 详情 | |
(V) | 12830 | (3,4-Diaminophenyl)phenylmethanone; 3,4-Diaminobenzophenone | 39070-63-8 | C13H12N2O | 详情 | 详情 |
(VI) | 39116 | (2-amino-1H-benzimidazol-6-yl)(phenyl)methanone | C14H11N3O | 详情 | 详情 | |
(VII) | 39117 | [2-amino-1-(isopropylsulfonyl)-1H-benzimidazol-6-yl](phenyl)methanone | C17H17N3O3S | 详情 | 详情 |