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【结 构 式】

【药物名称】

【化学名称】3,5-Dimethyl-4-(nitromethylsulfonyl)phenyl ester

【CA登记号】

【 分 子 式 】C10H10N2O4S2

【 分 子 量 】286.3302

【开发单位】University of Tennessee System (Originator)

【药理作用】ENDOCRINE DRUGS, Treatment of Diabetic Complications, Aldose Reductase Inhibitors

合成路线1

The acetylation of 3,5-dimethylaniline (I) with acetic anhydride gives the acetamide (II), which is treated with chlorosulfonic acid yielding the benzenesulfonyl chloride (III). The reduction of (III) with Na2SO3 and NaHCO3 in water affords the sulfinic acid (IV), which by reaction with sodium methoxide in methanol gives the corresponding sodium salt (V). The reaction of (V) with nitromethane and sodium methoxide yields the sulfonylnitromethane (VI), which is deacetylated with hot 2N NaOH affording 3,5-dimethyl-4-(nitromethylsulfonyl)aniline (VII). Finally, this compound is treated with thiophosgene in acetone to provide the target isothiocyanate.

1 Rodriguez, L.; Miller, D.D.; Kador, P.F.; Saab, N.H.; Donkor, I.O.; Phenylsulfonylnitromethasanes as potent irreversible inhibitors of aldose reductase. Eur J Med Chem 1999, 34, 9, 745.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
29008 Chlorosulfonic acid 7790-94-5 HClO3S 详情 详情
39563 nitromethane 75-52-5 CH3NO2 详情 详情
(I) 18431 3,5-dimethylaniline; 3,5-dimethylphenylamine 108-69-0 C8H11N 详情 详情
(II) 31521 N-(3,5-dimethylphenyl)acetamide C10H13NO 详情 详情
(III) 31596 4-(acetamido)-2,6-dimethylbenzenesulfonyl chloride C10H12ClNO3S 详情 详情
(IV) 31597 N-[4-(dioxo-lambda(6)-sulfanyl)-3,5-dimethylphenyl]acetamide C10H13NO3S 详情 详情
(V) 31598 [[4-(acetamido)-2,6-dimethylphenyl]sulfonyl]sodium C10H12NNaO3S 详情 详情
(VI) 31599 N-[3,5-dimethyl-4-[(nitromethyl)sulfonyl]phenyl]acetamide C11H14N2O5S 详情 详情
(VII) 31600 3,5-dimethyl-4-[(nitromethyl)sulfonyl]aniline; 3,5-dimethyl-4-[(nitromethyl)sulfonyl]phenylamine C9H12N2O4S 详情 详情
Extended Information