【结 构 式】 |
【分子编号】48246 【品名】N-benzyl-N,N-dipropyl-1-propanaminium chloride 【CA登记号】 |
【 分 子 式 】C16H28ClN 【 分 子 量 】269.85776 【元素组成】C 71.21% H 10.46% Cl 13.14% N 5.19% |
合成路线1
该中间体在本合成路线中的序号:(A)Condensation of 3,4,5-trichloro nitrobenzene (I) with 4-chlorobenzeneacetonitrile (II) by means of NaOH and N,N,N-triethylbenzylammonium chloride in THF yields substituted nitrobenzeneacetonitrile (III), which is subjected to hydrogenation over Pt/C in MeOH in the presence of thiophene to provide aniline (IV). Treatment of (IV) with HCl, HOAc and NaNO2, followed by reaction with ethyl N-(2-cyanoacetyl) carbamate (V) in AcOEt, furnishes ethyl carbamate derivative (VI), which is then subjected to cyclization by means of KOAc in refluxing HOAc to yield perhydro-3,5-dioxo-1,2,4-triazine derivative (VII). Hydrolysis of the nitrile moiety of (VII) by treatment with HCl in refluxing HOAc gives carboxylic acid (VIII), which is finally decarboxylated by heating in 2-mercaptoacetic acid to provide the desired product.
【1】 Boeckx, G.M.; Sipido, V.; Raeymaekers, A.H.M. (Janssen Pharmaceutica NV); alpha-Aryl-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetonitriles. AU 8545664; EP 0170316; ES 8609284; ES 8705403; JP 1986043176; JP 1993017454; US 4631278 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(B) | 13297 | Thiophene | 110-02-1 | C4H4S | 详情 | 详情 |
(A) | 48246 | N-benzyl-N,N-dipropyl-1-propanaminium chloride | C16H28ClN | 详情 | 详情 | |
(I) | 48245 | 1,2,3-trichloro-5-nitrobenzene | 20098-48-0 | C6H2Cl3NO2 | 详情 | 详情 |
(II) | 22871 | 2-(4-chlorophenyl)acetonitrile | 140-53-4 | C8H6ClN | 详情 | 详情 |
(III) | 48247 | 2-(4-chlorophenyl)-2-(2,6-dichloro-4-nitrophenyl)acetonitrile | C14H7Cl3N2O2 | 详情 | 详情 | |
(IV) | 48248 | 2-(4-amino-2,6-dichlorophenyl)-2-(4-chlorophenyl)acetonitrile | C14H9Cl3N2 | 详情 | 详情 | |
(V) | 48249 | ethyl 2-cyanoacetylcarbamate | C6H8N2O3 | 详情 | 详情 | |
(VI) | 48250 | ethyl 2-cyano-2-((Z)-2-[3,5-dichloro-4-[(4-chlorophenyl)(cyano)methyl]phenyl]hydrazono)acetylcarbamate | C20H14Cl3N5O3 | 详情 | 详情 | |
(VII) | 48251 | 2-[3,5-dichloro-4-[(4-chlorophenyl)(cyano)methyl]phenyl]-3,5-dioxo-1,2,4-triazinane-6-carbonitrile | C18H10Cl3N5O2 | 详情 | 详情 | |
(VIII) | 48252 | 2-[3,5-dichloro-4-[(4-chlorophenyl)(cyano)methyl]phenyl]-3,5-dioxo-1,2,4-triazinane-6-carboxylic acid | C18H11Cl3N4O4 | 详情 | 详情 | |
(C) | 12893 | Ethanethioic S-acid | C2H4OS | 详情 | 详情 |