(4-chlorophenyl)methanethiol; 4-chlorobenzylhydrosulfide -Drug Synthesis Database

【结构式】

【分子编号】32674

【品名】(4-chlorophenyl)methanethiol; 4-chlorobenzylhydrosulfide

【CA登记号】6258-66-8

【分子式】C₇H₇ClS

【分子量】158.65128

【元素组成】C 52.99% H 4.45% Cl 22.35% S 20.21%

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：(V)

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

合成路线2

该中间体在本合成路线中的序号：(II)

Condensation of the known chloro pyrazolopyridine (I) with the lithium salt of 4-chlorobenzylthiol (II) produces the intermediate thioether (III) which, in the presence of excess LDA, undergoes intramolecular Claisen condensation to the pyrazolothienopyridine derivative (IV). Subsequent acylation of (IV) with glutaric anhydride (V) in acetone gives rise to the target glutarate mono-ester.

参考文献中间体

合成目标

【1】 da Silva, K.C.M.; Fraga, C.A.M.; Barreiro, E.J.; de Brito, F.C.F.; de Miranda, A.L.P.; Cardoso, C.R.; Design, synthesis and pharmacological evaluation of novel pyrazolo[3,4-b]thieno[2,3-d]pyridine acid derivatives: A new class of anti-inflammatory and anti-platelet agents. Bioorg Med Chem Lett 2002, 12, 1, 9.

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)	57506	ethyl 4-chloro-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate		C₁₆H₁₄ClN₃O₂	详情	详情
(II)	32674	(4-chlorophenyl)methanethiol; 4-chlorobenzylhydrosulfide	6258-66-8	C₇H₇ClS	详情	详情
(III)	52507	6-chloro-2-nitro-9-oxo-9,10-dihydro-4-acridinecarboxylic acid		C₁₄H₇ClN₂O₅	详情	详情
(IV)	57508	2-(4-chlorophenyl)-8-methyl-6-phenyl-6H-pyrazolo[3,4-b]thieno[2,3-d]pyridin-3-ol		C₂₁H₁₄ClN₃OS	详情	详情
(V)	15512	Glutaric Anhydride; dihydro-2H-pyran-2,6(3H)-dione	108-55-4	C₅H₆O₃	详情	详情

Extended Information