4-(3-chloro-1-phenyl-1H-pyrazol-5-yl)phenyl methyl sulfide; 3-chloro-5-[4-(methylsulfanyl)phenyl]-1-phenyl-1H-pyrazole -Drug Synthesis Database

【结构式】

【分子编号】52014

【品名】4-(3-chloro-1-phenyl-1H-pyrazol-5-yl)phenyl methyl sulfide; 3-chloro-5-[4-(methylsulfanyl)phenyl]-1-phenyl-1H-pyrazole

【CA登记号】

【分子式】C₁₆H₁₃ClN₂S

【分子量】300.8114

【元素组成】C 63.89% H 4.36% Cl 11.79% N 9.31% S 10.66%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(V)

The cyclization of phenylhydrazine (I) with 3-[4-(methylsulfanyl)phenyl]acrylonitrile (II) by means of NaOEt in refluxing ethanol gives the aminopyrazoline (III), which is dehydrogenated by means of MnO2 in dichloromethane to yield the 3-aminopyrazole (IV). The diazotation of (IV) with NaNO2 and HCl in water, followed by a treatment with Cu2Cl2, affords the 3-chloropyrazole (V), which is finally oxidized to the target sulfone by means of MCPBA in dichloromethane.

参考文献中间体

合成目标

【1】 Matsuo, M.; Okumura, K.; Ogino, T.; Nakamura, K.; Nishimura, H.; Harada, K.; Hotta, Y.; Tsuji, K. (Fujisawa Pharmaceutical Co., Ltd.); 1,3,5-Trisubstd. pyrazoles for treatment of inflammation. EP 0856000; JP 1999513403; WO 9713755 .

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)	11818	Phenyl hydrazine; 1-Phenylhydrazine	100-63-0	C₆H₈N₂	详情	详情
(II)	52011	(E)-3-[4-(methylsulfanyl)phenyl]-2-propenenitrile		C₁₀H₉NS	详情	详情
(III)	52012	5-[4-(methylsulfanyl)phenyl]-1-phenyl-4,5-dihydro-1H-pyrazol-3-amine; 5-[4-(methylsulfanyl)phenyl]-1-phenyl-4,5-dihydro-1H-pyrazol-3-ylamine		C₁₆H₁₇N₃S	详情	详情
(IV)	52013	5-[4-(methylsulfanyl)phenyl]-1-phenyl-1H-pyrazol-3-ylamine; 5-[4-(methylsulfanyl)phenyl]-1-phenyl-1H-pyrazol-3-amine		C₁₆H₁₅N₃S	详情	详情
(V)	52014	4-(3-chloro-1-phenyl-1H-pyrazol-5-yl)phenyl methyl sulfide; 3-chloro-5-[4-(methylsulfanyl)phenyl]-1-phenyl-1H-pyrazole		C₁₆H₁₃ClN₂S	详情	详情

Extended Information