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【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%

与该中间体有关的原料药合成路线共 2 条

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
Extended Information