【结 构 式】 |
【分子编号】14486 【品名】4-Chloro-3-nitrobenzoylchloride; 4-chloro-3-nitrobenzoyl chloride 【CA登记号】38818-50-7 |
【 分 子 式 】C7H3Cl2NO3 【 分 子 量 】220.01116 【元素组成】C 38.21% H 1.37% Cl 32.23% N 6.37% O 21.82% |
合成路线1
该中间体在本合成路线中的序号:(II)The reaction of 4-chloro-3-nitrobenzoic acid (I) with thionyl chloride gives the acid chloride (II) which, by reaction with 4-methylpiperidine, affords the amide (III). Amination of (III) with methanolic ammonia followed by reduction of the nitro group gives the diamine compound (IV), which reacts with 1,3-bis(methoxycarbonyl)-S-methylisothiourea affording CDRI-87-144.
【1】 Beard, C.C. (Syntex (USA), Inc.); 5(6)-Benzene ring substd. benzimidazole-2-carbamate derivs. having anthelmintic activity. US 4086235 . |
【2】 Arya, V.P.; CDRI-87-144. Drugs Fut 1991, 16, 5, 420. |
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) | 14485 | 3-nitro-4-chlorobenzoic acid; 4-chloro-3-nitrobenzoic acid | 96-99-1 | C7H4ClNO4 | 详情 | 详情 |
(II) | 14486 | 4-Chloro-3-nitrobenzoylchloride; 4-chloro-3-nitrobenzoyl chloride | 38818-50-7 | C7H3Cl2NO3 | 详情 | 详情 |
(III) | 14487 | (4-chloro-3-nitrophenyl)(4-methylpiperidino)methanone | C13H15ClN2O3 | 详情 | 详情 | |
(IV) | 14488 | (3,4-diaminophenyl)(4-methylpiperidino)methanone | C13H19N3O | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(II)The Friedel Krafts reaction of fluorobenzene (I) and 3-nitro-4-chlorobenzoyl chloride (II) by means of AlCl3 gives 3-nitro-4-chloro-4’-fluorobenzophenone (III), which by reaction with NH3 in ethylenglycol at 130 C yields 3-nitro-4-amino-4’-fluorobenzophenone (IV). The reduction of (IV) with H2 over Pd/C in methanol affords 3,4-diamino-4’-fluorobenzophenone (V), which is finally cyclized with S-methylthiourea (VI) and methyl chloroformate by means of NaOH in water
【1】 Tan, K.; Duquette, M.; Liu, J.H.; Dong, Y.; Zhang, R.; Joachimiak, A.; Lawler, J.; Wang, J.H.; Crystal structure of the TSP-1 type 1 repeats: A novel layered fold and its biological implication. Arzneim-Forsch Drug Res 1978, 28, 4, 586. |
【2】 Van Gelder, J.L.H.; et al. (Janssen Pharmaceutica NV); BE 752089; DE 2029637; FR 2052988; GB 1307306; US 3657267; ZA 7004191 . |
【3】 Castaner, J.; Bogan, J.A.; Flubendazole.. Drugs Fut 1978, 3, 10, 739. |
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) | 17466 | Fluorobenzene | 462-06-6 | C6H5F | 详情 | 详情 |
(II) | 14486 | 4-Chloro-3-nitrobenzoylchloride; 4-chloro-3-nitrobenzoyl chloride | 38818-50-7 | C7H3Cl2NO3 | 详情 | 详情 |
(III) | 60714 | (4-chloro-3-nitrophenyl)(4-fluorophenyl)methanone | C13H7ClFNO3 | 详情 | 详情 | |
(IV) | 60715 | (4-amino-3-nitrophenyl)(4-fluorophenyl)methanone | C13H9FN2O3 | 详情 | 详情 | |
(V) | 60716 | (3,4-diaminophenyl)(4-fluorophenyl)methanone | C13H11FN2O | 详情 | 详情 | |
(VI) | 10272 | [[Amino(imino)methyl]sulfanyl]methane | 2986-19-8 | C2H6N2S | 详情 | 详情 |