N~1~,N~1~-bis(2-chloroethyl)-1,4-benzenediamine; N-(4-aminophenyl)-N,N-bis(2-chloroethyl)amine -Drug Synthesis Database

【结构式】

【分子编号】64082

【品名】N~1~,N~1~-bis(2-chloroethyl)-1,4-benzenediamine; N-(4-aminophenyl)-N,N-bis(2-chloroethyl)amine

【CA登记号】

【分子式】C₁₀H₁₄Cl₂N₂

【分子量】233.14004

【元素组成】C 51.52% H 6.05% Cl 30.41% N 12.02%

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：(VII)

In an alternative method, p-nitroaniline (I) is reacted with ethylene oxide (II) to afford diol (III). This compound can also be prepared by condensation of 1-fluoro-4-nitrobenzene (IV) with diethanolamine (V). Chlorination of diol (III) to provide (VI) is accomplished with either mesyl chloride or SOCl2 in the presence of pyridine. Then, nitro group reduction in (VI) by means of iron and HCl affords aniline (VII).

参考文献中间体

合成目标

【1】 Jordan, A.M.; Khan, T.H.; Malkin, H.; Osborn, H.M.I.; Synthesis and analysis of urea and carbamate prodrugs as candidates for melanocyte-directed enzyme prodrug therapy (MDEPT). Bioorg Med Chem 2002, 10, 8, 2625.

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)	15547	4-nitrophenylamine; p-Nitroaniline; 4-nitroaniline	100-01-6	C₆H₆N₂O₂	详情	详情
(II)	10393	Oxirane; Ethylene oxide	75-21-8	C₂H₄O	详情	详情
(III)	64080	2-[(2-hydroxyethyl)-4-nitroanilino]-1-ethanol		C₁₀H₁₄N₂O₄	详情	详情
(IV)	14153	4-Fluoronitrobenzene; 1-Fluoro-4-nitrobenzene	350-46-9	C₆H₄FNO₂	详情	详情
(V)	24273	2-[(2-hydroxyethyl)amino]-1-ethanol	111-42-2	C₄H₁₁NO₂	详情	详情
(VI)	64081	N,N-bis(2-chloroethyl)-4-nitroaniline; N,N-bis(2-chloroethyl)-N-(4-nitrophenyl)amine		C₁₀H₁₂Cl₂N₂O₂	详情	详情
(VII)	64082	N~1~,N~1~-bis(2-chloroethyl)-1,4-benzenediamine; N-(4-aminophenyl)-N,N-bis(2-chloroethyl)amine		C₁₀H₁₄Cl₂N₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VII)

Reaction of tyramine (VIII) with p-nitrophenyl chloroformate (IX) gives rise to the nitrophenyl carbamate (X). Finally, coupling of (X) with aniline (VII) provides the title urea.

参考文献中间体

合成目标

【1】 Jordan, A.M.; Khan, T.H.; Malkin, H.; Osborn, H.M.I.; Synthesis and analysis of urea and carbamate prodrugs as candidates for melanocyte-directed enzyme prodrug therapy (MDEPT). Bioorg Med Chem 2002, 10, 8, 2625.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VII)	64082	N~1~,N~1~-bis(2-chloroethyl)-1,4-benzenediamine; N-(4-aminophenyl)-N,N-bis(2-chloroethyl)amine		C₁₀H₁₄Cl₂N₂	详情	详情
(VIII)	19988	4-(2-Aminoethyl)phenol; Tyramine	51-67-2	C₈H₁₁NO	详情	详情
(IX)	16605	4-Nitrophenyl chloroformate; 1-[(Chlorocarbonyl)oxy]-4-nitrobenzene	7693-46-1	C₇H₄ClNO₄	详情	详情
(X)	64083	4-nitrophenyl 4-hydroxyphenethylcarbamate		C₁₅H₁₄N₂O₅	详情	详情

Extended Information