2,2',4'-trichloroacetophenone; 2-chloro-1-(2,4-dichlorophenyl)-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】31092

【品名】2,2',4'-trichloroacetophenone; 2-chloro-1-(2,4-dichlorophenyl)-1-ethanone

【CA登记号】4252-78-2

【分子式】C₈H₅Cl₃O

【分子量】223.4852

【元素组成】C 43% H 2.26% Cl 47.59% O 7.16%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

The reduction of 2,4-dichlorophenacyl chloride with NaBH4 gives 1-(2,4-dichlorophenyl)-2-chloroethanol (II), which is condensed with imidazole (III) to yield 1-(2,4-dichlorophenyl)-2-(N-imidazolyl)ethanol (IV). Finally, this compound is condensed with 4-(phenylthio)benzyl chloride (V) [prepared by chloromethylation of diphenyl sulfide (VI) with formaldehyde and HCl] using NaH as condensing agent.

参考文献中间体

合成目标

【1】 Cova, A.; Tajana, A.; Nardi, D.; Cappelleti, R.; Sibilia, C.; Physico-chemical, structural and analytical studies on fenticonazole, a new drug with antimycotic properties. Arzneim-Forsch Drug Res 1981, 31, 12, 2127.
【2】 Nardi, D.; Massarani, E.; Tajana, A.; Veronese, M. (Recordati Industria Chimica e Farmaceutica SpA); Substituted dibenzyl ethers and parmaceutical compositions containing said ethers for the treatment of infections. DE 2917244; FR 2426047; GB 2025395; US 4221803 .
【3】 Blancafort, P.; Castaner, J.; Serradell, M.N.; Fenticonazole Nitrate. Drugs Fut 1983, 8, 9, 767.

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)	31092	2,2',4'-trichloroacetophenone; 2-chloro-1-(2,4-dichlorophenyl)-1-ethanone	4252-78-2	C₈H₅Cl₃O	详情	详情
(II)	31093	2-chloro-1-(2,4-dichlorophenyl)-1-ethanol	13692-14-3	C₈H₇Cl₃O	详情	详情
(III)	10255	Imidazole; 1H-Imidazole	288-32-4	C₃H₄N₂	详情	详情
(IV)	14550	1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-1-ethanol; alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol; 1-(2',4'-Dichlorophenyl)-2-(1-imidazolyl)ethanol	24155-42-8	C₁₁H₁₀Cl₂N₂O	详情	详情
(V)	31094	1-(chloromethyl)-4-(phenylsulfanyl)benzene; 4-(chloromethyl)phenyl phenyl sulfide		C₁₃H₁₁ClS	详情	详情
(VI)	23188	1-(phenylsulfanyl)benzene; diphenyl sulfide	139-66-2	C₁₂H₁₀S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The reaction of 2,4-dichlorophenacyl chloride (I) with imidazole (A) gives the ketone (II), which is reduced with sodium borohydride to yield the alcohol (III). Conversion of the alcohol (III) to the chloro derivative (IV) with thionylchloride followed by reaction with p-chlorobenzyl mercaptan (V) affords sulconazole.

参考文献中间体

合成目标

【1】 Keisu, E.E. U.; Manufacture of novel imidazole derivative. AT 347449B; BE 0833614; JP 59089667; ZA 7505100 .
【2】 Arya, V.P.; Sulconazole. Drugs Fut 1980, 5, 4, 206.

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)	10255	Imidazole; 1H-Imidazole	288-32-4	C₃H₄N₂	详情	详情
(I)	31092	2,2',4'-trichloroacetophenone; 2-chloro-1-(2,4-dichlorophenyl)-1-ethanone	4252-78-2	C₈H₅Cl₃O	详情	详情
(II)	32200	1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-1-ethanone	46503-52-0	C₁₁H₈Cl₂N₂O	详情	详情
(III)	14550	1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-1-ethanol; alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol; 1-(2',4'-Dichlorophenyl)-2-(1-imidazolyl)ethanol	24155-42-8	C₁₁H₁₀Cl₂N₂O	详情	详情
(IV)	32673	1-[2-chloro-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole		C₁₁H₉Cl₃N₂	详情	详情
(V)	32674	(4-chlorophenyl)methanethiol; 4-chlorobenzylhydrosulfide	6258-66-8	C₇H₇ClS	详情	详情

Extended Information