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【结 构 式】

【分子编号】39059

【品名】(1,3,4-triphenyl-1H-pyrazol-5-yl)methanol

【CA登记号】

【 分 子 式 】C22H18N2O

【 分 子 量 】326.3978

【元素组成】C 80.96% H 5.56% N 8.58% O 4.9%

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:(VIII)

The reaction of aniline (I) with ethyl bromoacetate (II) by means of triethylamine in benzene gives ethyl phenylaminoacetate (III), which is nitrosated with NaNO2 and HCl in water to yield ethyl N-nitrosophenylaminoacetate (IV). The reduction of (IV) with Zn in ethanol-water-acetic anhydride affords ethyl N1-phenylhydrazinoacetate (V), which is condensed with benzil (A) by means of HCl-sodium acetate in refluxing ethanol-water to yield ethyl alpha-benzoylbenzylidene-N1-phenylhydrazinoacetate (VI). The cyclization of (VI) by means of sodium ethoxide in refluxing ethanol gives 1,3,4-triphenylpyrazole-5-carboxylic acid (VII), which is reduced with LiAlH4 in ether-THF to produce 1,3,4-triphenyl-5-(hydroxymethyl)pyrazole (VIII). The reaction of (VIII) with SOCl2 in refluxing chloroform yields 1,3,4-triphenyl-5-(chloromethyl)pyrazole (IX), which by reaction with NaCN in hot DMSO is converted into 1,3,4-triphenylpyrazole-5-acetonitrile (X). Finally, this compound is hydrolyzed by means of NaOH in refluxing aqueous ethanol.

1 Gueremy, C.; Renault, C.; US 3984431 .
2 Castaner, J.; Arrigoni, Martelli, E.; Isofezolac. Drugs Fut 1980, 5, 1, 21.
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) 39056 Dibenzoyl; benzil 134-81-6 C14H10O2 详情 详情
(I) 12294 Aniline; Phenylamine 62-53-3 C6H7N 详情 详情
(II) 16640 Ethyl 2-bromoacetate; Ethyl bromoacetate 105-36-2 C4H7BrO2 详情 详情
(III) 25701 ethyl 2-anilinoacetate 2216-92-4 C10H13NO2 详情 详情
(IV) 39055   C10H12N2O3 详情 详情
(V) 25702 ethyl 2-(1-phenylhydrazino)acetate C10H14N2O2 详情 详情
(VI) 39057 ethyl (Z)-4-oxo-3,4-diphenyl-2-(1-phenylhydrazino)-2-butenoate C24H22N2O3 详情 详情
(VII) 39058 1,3,4-triphenyl-1H-pyrazole-5-carboxylic acid C22H16N2O2 详情 详情
(VIII) 39059 (1,3,4-triphenyl-1H-pyrazol-5-yl)methanol C22H18N2O 详情 详情
(IX) 39060 5-(chloromethyl)-1,3,4-triphenyl-1H-pyrazole C22H17ClN2 详情 详情
(X) 39061 2-(1,3,4-triphenyl-1H-pyrazol-5-yl)acetonitrile C23H17N3 详情 详情
Extended Information