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【结 构 式】

【分子编号】12103

【品名】N-[2-Bromo-5-(trifluoromethyl)phenyl]ethanethioamide

【CA登记号】

【 分 子 式 】C9H7BrF3NS

【 分 子 量 】298.1265296

【元素组成】C 36.26% H 2.37% Br 26.8% F 19.12% N 4.7% S 10.76%

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:(IX)

5) Esterified intermediate (IV) can also be obtained as follows: The reaction of 2-bromo-5-(trifluoromethyl)acetanilide (VIII) with phosphorus pentasulfide in refluxing benzene gives the corresponding thioamide (IX), which is cyclized by means of NaH in hot N-methylpyrrolidone yielding 2-methyl-5-(trifluoromethyl)benzothiazole (X). The bromination of (X) with N-bromosuccinimide (NBS) and benzoyl peroxide in refluxing CCl4 affords the corresponding bromomethyl derivative (XI), which is then condensed with phthalazinone (I) by means of NaH in DMF.

1 Mealy, N.; Prous, J.; Castaner, J.; Zopolrestat. Drugs Fut 1995, 20, 1, 33.
2 Mylari, B.L.; Zembrowski, W.J.; Synthesis of aldose reductase inhibitor, 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2 14C benzothiazolyl]methyl]-1-phthalazineacetic acid. J Label Compd Radiopharm 1991, 29, 2, 143-8.
3 Mylari, B.L.; Larson, E.R.; Zembrowski, W.J. (Pfizer Inc.); Heterocyclic oxophthalazinylacetic acids. EP 0222576; JP 1987114988; US 4939140 .
4 Mylari, B.L.; Zembrowski, W.J. (Pfizer Inc.); Preparation of oxophthalazinyl acetic acids having benzothiazole or other heterocyclic side chains. EP 0295051 .
5 Siegel, T.W.; Aldinger, C.E.; Mylari, B.L.; Singleton, D.H.; Zembrowski, W.J.; Larson, E.R.; Beyer, T.A.; Dee, M.F.; Novel, potent aldose reductase inhibitors: 3,4-Dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1-phthalazine-acetic acid (zopolrestat) and congeners. J Med Chem 1991, 34, 1, 108-22.
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) 12095 ethyl 2-(4-oxo-3,4-dihydro-1-phthalazinyl)acetate; Ethyl 3,4-dihydro-4-oxo-1-phthalazineacetate 25947-13-1 C12H12N2O3 详情 详情
(IV) 23855 2-(4-oxo-3-[[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]methyl]-3,4-dihydro-1-phthalazinyl)acetic acid C19H12F3N3O3S 详情 详情
(VIII) 12102 N-[2-Bromo-5-(trifluoromethyl)phenyl]acetamide C9H7BrF3NO 详情 详情
(IX) 12103 N-[2-Bromo-5-(trifluoromethyl)phenyl]ethanethioamide C9H7BrF3NS 详情 详情
(X) 12104 2-Methyl-5-(trifluoromethyl)-1,3-benzothiazole 398-99-2 C9H6F3NS 详情 详情
(XI) 12105 2-(Bromomethyl)-5-(trifluoromethyl)-1,3-benzothiazole C9H5BrF3NS 详情 详情
Extended Information