1-(phenylsulfanyl)benzene; diphenyl sulfide -Drug Synthesis Database

【结构式】

【分子编号】23188

【品名】1-(phenylsulfanyl)benzene; diphenyl sulfide

【CA登记号】139-66-2

【分子式】C₁₂H₁₀S

【分子量】186.2774

【元素组成】C 77.37% H 5.41% S 17.21%

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：(VI)

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：(II)

The reaction of 2-phenyl-2,3,5,6,7,8-hexahydro imidazo[1,2-a]pyridine (I) with diphenyl sulfide (II) by means of n-butyllithium in THF gives 2-phenyl-8-(phenylthio)-2,3,5,6,7,8-hexahydroimidazo[1,2-a]pyridine (III), which is then oxidized with chloramine T in methanol and simultaneously ketalized.

参考文献中间体

合成目标

【1】 Murray, R.J.; Loch, J.T. III; Radov, L.A.; Davidson, T.A.; Kamp, D.; Trusso, L.A.; Gawlack, D.L.; Immunomodulatory pyrrolo[1,2-a]imidazoles and imidazol[1,2-a]pyridines. 192nd ACS Natl Meet (Sept 7-12, Anaheim) 1986, Abst MEDI-81.
【2】 Davidson, T.A.; Murray, R.J. (Pennwalt Corp.); Pyrrolo[1,2-a]imidazole and imidazo[1,2-a]pyridine. EP 0150255; US 4507481 .
【3】 Castaner, J.; Prous, J.; PR-879317A. Drugs Fut 1988, 13, 10, 934.

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)	23187	2-phenyl-2,3,5,6,7,8-hexahydroimidazo[1,2-a]pyridine		C₁₃H₁₆N₂	详情	详情
(II)	23188	1-(phenylsulfanyl)benzene; diphenyl sulfide	139-66-2	C₁₂H₁₀S	详情	详情
(III)	23189	phenyl 2-phenyl-2,3,5,6,7,8-hexahydroimidazo[1,2-a]pyridin-8-yl sulfide; 2-phenyl-8-(phenylsulfanyl)-2,3,5,6,7,8-hexahydroimidazo[1,2-a]pyridine		C₁₉H₂₀N₂S	详情	详情

Extended Information