【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% |
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 |