N-hydroxybenzamide -Drug Synthesis Database

【结构式】

【分子编号】24777

【品名】N-hydroxybenzamide

【CA登记号】495-18-1

【分子式】C₇H₇NO₂

【分子量】137.13812

【元素组成】C 61.31% H 5.14% N 10.21% O 23.33%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

The reaction of benzohydroxamic acid (I) with benzyl bromide (II) by means of NaOH on ethanol gives the corresponding benzyl ester (III), which is treated with HCl yielding O-benzylhydroxylamine (IV). The reaction of (IV) with dicyaniamide (V) in ethanol affords the biguanide (VI), which is cyclized with cyclopentanone (VII) and HCl giving 1-benzyloxy-2,2-dimethyl-1,2-dihydro-1,3,5-triazine-4,6-diamine (VIII). The debenzylation of (VIII) with H2 over PtO2 in ethanol yields 1-hydroxy-2,2-dimethyl-1,2-dihydro-1,3,5-triazine-4,6-diamine (IX), which is finally condensed with 1,6-dibromohexane (X) by means of NaOH in methanol.

参考文献中间体

合成目标

【1】 Zhang, X.P.; Shen, J.; Xin, Z.M.; Qiu, Q.P.; Zhou, W.C.; Synthesis and antiprotozoal activities of some new triazine derivatives including a new antitrypanosomal agent: SIPI-1029. Acta Pharm Sin 1996, 31, 11, 823.
【2】 Zhou, W.; Zhang, X.; Trybizine Hydrochloride. Drugs Fut 1999, 24, 10, 1084.

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)	24777	N-hydroxybenzamide	495-18-1	C₇H₇NO₂	详情	详情
(II)	12912	1-(Bromomethyl)benzene; Alpha-bromotoluene	100-39-0	C₇H₇Br	详情	详情
(III)	24779	N-(benzyloxy)benzamide		C₁₄H₁₃NO₂	详情	详情
(IV)	14640	O-benzylhydroxylamine; 1-[(aminooxy)methyl]benzene	622-33-3	C₇H₉NO	详情	详情
(V)	23611	N-cyanoguanidine	461-58-5	C₂H₄N₄	详情	详情
(VI)	24782	1-[([[[[amino(imino)methyl]amino](imino)methyl]amino]oxy)methyl]benzene		C₉H₁₃N₅O	详情	详情
(VII)	15113	cyclopentanone	120-92-3	C₅H₈O	详情	详情
(VIII)	24784	10-(benzyloxy)-6,8,10-triazaspiro[4.5]deca-6,8-diene-7,9-diamine		C₁₄H₁₉N₅O	详情	详情
(IX)	24785	7,9-diamino-6,8,10-triazaspiro[4.5]deca-7,9-dien-6-ol		C₇H₁₃N₅O	详情	详情
(X)	24786	1,6-dibromohexane	629-03-8	C₆H₁₂Br₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The reaction of benzohydroxamic acid (I) with 1,6-dibromohexane (X) by means of NaOH in methanol gives the bis benzohydroxamic ester (XI), which is treated with HCl to afford the subituted bis hydroxylamine (XII). The reaction of (XII) with dicyandiamide (V) in ethanol yields the bis biguanide (XIII), which is finally cyclized with cyclopentanone (VII) and HCl as before.

参考文献中间体

合成目标

【1】 Zhang, X.P.; Shen, J.; Xin, Z.M.; Qiu, Q.P.; Zhou, W.C.; Synthesis and antiprotozoal activities of some new triazine derivatives including a new antitrypanosomal agent: SIPI-1029. Acta Pharm Sin 1996, 31, 11, 823.
【2】 Zhou, W.; Zhang, X.; Trybizine Hydrochloride. Drugs Fut 1999, 24, 10, 1084.

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)	24777	N-hydroxybenzamide	495-18-1	C₇H₇NO₂	详情	详情
(V)	23611	N-cyanoguanidine	461-58-5	C₂H₄N₄	详情	详情
(VII)	15113	cyclopentanone	120-92-3	C₅H₈O	详情	详情
(X)	24786	1,6-dibromohexane	629-03-8	C₆H₁₂Br₂	详情	详情
(XI)	24787	N-([6-[(benzoylamino)oxy]hexyl]oxy)benzamide		C₂₀H₂₄N₂O₄	详情	详情
(XII)	24788	1,6-bis(aminooxy)hexane		C₆H₁₆N₂O₂	详情	详情
(XIII)	24789	1,6-bis([[[[amino(imino)methyl]amino](imino)methyl]amino]oxy)hexane		C₁₀H₂₄N₁₀O₂	详情	详情

Extended Information