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【结 构 式】

【分子编号】59303

【品名】N-(2-nitro-4-propoxyphenyl)acetamide

【CA登记号】

【 分 子 式 】C11H14N2O4

【 分 子 量 】238.24324

【元素组成】C 55.46% H 5.92% N 11.76% O 26.86%

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:(III)

Alkylation of 4-hydroxyacetanilide (I) with n-propyl bromide provided 4-propoxyacetanilide (II). Aromatic nitration of (II) with fuming nitric acid in the presence of acetic anhydride afforded the nitro acetanilide (III), which was further hydrolyzed to the nitro aniline (IV) under basic conditions. Subsequent catalytic hydrogenation of the nitro group of (IV) furnished the phenylenediamine (V). Cyanocarbamate (VI), generated from cyanamide and methyl chloroformate, was then condensed with 4-propoxy-1,2-phenylenediamine (V) in hot pyridine to provide the title benzimidazolyl carbamate.

1 Castaner, J.; Bogan, J.A.; Oxibendazole. Drugs Fut 1976, 1, 5, 255.
2 Actor, P.P.; Pagano, J.F. (GlaxoSmithKline Inc.); Anthelmintic compsns. and methods employing esters of benzimidazolyl carbamic acids and their thio analogs. BE 0666795; BE 0691611; CH 479590; DE 1620439; DE 1795799; FR 1510235; GB 1096190; GB 1114069; GB 1123317; US 3574845 .
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) 21611 4'-Hydroxyacetanilide;4-Acetamidophenol;N-Acetyl-4-aminophenol;Paracetamol;Acetaminophen;p-Hydroxyacetanilide; Paracetamol; N-(4-hydroxyphenyl)acetamide 103-90-2 C8H9NO2 详情 详情
(II) 59302 N-(4-propoxyphenyl)acetamide C11H15NO2 详情 详情
(III) 59303 N-(2-nitro-4-propoxyphenyl)acetamide C11H14N2O4 详情 详情
(IV) 59304 2-nitro-4-propoxyaniline; 2-nitro-4-propoxyphenylamine C9H12N2O3 详情 详情
(V) 59305 2-amino-4-propoxyphenylamine; 4-propoxy-1,2-benzenediamine C9H14N2O 详情 详情
(VI) 33600 methyl cyanocarbamate C3H4N2O2 详情 详情
Extended Information