Oxibendazole, SK&F-30310, Filaribits Plus, Anthelcide EQ
奥苯达唑Chemical Name: N-(5-Propoxy-1H-benzimidazol-2-yl)carbamic acid methyl ester
CAS No. 20559-55-1
项目整合开发状态: Phase III
项目研究机构: GlaxoSmithKline (Originator)
合成路线: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.
📌 参考资料/链接：
参考文献标题:Anthelmintic compsns.and methods employing esters of benzimidazolyl carbamic acids and their thio analogs
文献作者:Actor,P.P.; Pagano,J.F.(GlaxoSmithKline Inc.)
参考来源:BE 0666795; BE 0691611; CH 479590; DE 1620439; DE 1795799; FR 1510235; GB 1096190; GB 1114069; GB 1123317; US 3574845
📄 详细内容
合成路线:An new process for the preparation of the precursor phenylenediamine (V) has been reported.The previously reported 5-chlorobenzimidazole-2-spirocyclohexane (VII) was treated with sodium propoxide to yield the propoxy derivative (VIII).Sodium dithionite reduction of (VIII) gave rise to the target phenylenediamine (V) via intermediate (IX).Then,condensation of diamine (V) with cyanamide and methyl chloroformate produced the target benzimidazole derivative.
参考文献标题:2H-Benzimidazoles (isobenzimidazoles).Part 10.Synthesis of polysubstituted o-phenylenediamines and their conversion into heterocycles,particularly 2-substituted benzimidazoles with known or potential anthelmintic activity
文献作者:Hazelton,J.C.; et al.
参考来源:Tetrahedron 1995,51(39),10771
合成路线: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.
参考文献标题:Oxibendazole
文献作者:Castar,J.; Bogan,J.A.
参考来源:Drugs Fut 1976,1(5),255
产品链接: CAS No. 20559-55-1››