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【结 构 式】

【分子编号】40954

【品名】methyl 5-(diethylamino)-1-(4-nitrophenyl)pentylcarbamate

【CA登记号】

【 分 子 式 】C17H27N3O4

【 分 子 量 】337.4192

【元素组成】C 60.51% H 8.07% N 12.45% O 18.97%

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 condensation of 4-nitrophenylacetonitrile (I) with diethyl carbonate by means of sodium ethylate in toluene gave the intermediate arylcyanoacetate sodium salt (II) that was further alkylated with 1,4-dibromobutane (III) to yield the bromobutyl derivative (IV). Subsequent treatment of bromide (IV) with diethylamine provided amine (V). Decarbethoxylation of the cyanoester group of (V) to give (VI) was carried out using aqueous KOH in the presence of benzyltriethylammonium chloride. Partial hydrolysis of the nitrile group of (VI) by means of potassium hydroperoxide in DMSO afforded amide (VII). This was subjected to Hoffman rearrangement by means of Br2 and NaOEt to produce carbamate (VIII), which was subsequently hydrolyzed to amine (IX) with KOH. This was finally coupled with benzoyl chloride to furnish the title benzamide.

1 L'vov, A.I.; Davydova, N.K.; Sizova, O.S.; Glushov, R.G.; Mashkovskiy, M.D.; Vinogradova, S.M.; Yurhakov, S.D.; Synthesis and antifibrillatory activity of nibentan and its analogues. Eur J Med Chem 2000, 35, 2, 205.
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) 40948 2-(4-nitrophenyl)acetonitrile 555-21-5 C8H6N2O2 详情 详情
(II) 40949   C11H9N2NaO4 详情 详情
(III) 11883 1,4-Dibromobutane; 1,4-Butylene bromide 110-52-1 C4H8Br2 详情 详情
(IV) 40950 ethyl 6-bromo-2-cyano-2-(4-nitrophenyl)hexanoate C15H17BrN2O4 详情 详情
(V) 40951 ethyl 2-cyano-6-(diethylamino)-2-(4-nitrophenyl)hexanoate C19H27N3O4 详情 详情
(VI) 40952 6-(diethylamino)-2-(4-nitrophenyl)hexanenitrile C16H23N3O2 详情 详情
(VII) 40953 6-(diethylamino)-2-(4-nitrophenyl)hexanamide C16H25N3O3 详情 详情
(VIII) 40954 methyl 5-(diethylamino)-1-(4-nitrophenyl)pentylcarbamate C17H27N3O4 详情 详情
(IX) 40955 N-[5-amino-5-(4-nitrophenyl)pentyl]-N,N-diethylamine; N(5),N(5)-diethyl-1-(4-nitrophenyl)-1,5-pentanediamine C15H25N3O2 详情 详情
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