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【结 构 式】 
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【分子编号】28301 【品名】1,5-dichloro-2-nitro-4-(trifluoromethyl)benzene 【CA登记号】400-70-4 |
【 分 子 式 】C7H2Cl2F3NO2 【 分 子 量 】259.9990296 【元素组成】C 32.34% H 0.78% Cl 27.27% F 21.92% N 5.39% O 12.31% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of 2,4-dichloro-5-(trifluoromethyl)nitrobenzene (I) with aminomethanephosphonic acid (II) by means of NaOH in ethanol/water gives the anilinomethanephosphonic acid (III), which is condensed first with morpholine (IV) by heating at 120 C and esterified with triethyl orthoformate at 150 C yielding 5-(4-morpholinyl)-2-nitro-4-(trifluoromethyl)phenylaminomethyl phosphonic acid diethyl ester (V). The reduction of the nitro group of (V) with H2 over Pd/C in ethanol affords the corresponding amino-derivative (VI), which is cyclized with oxalic acid monoethyl ester monochloride (VII) by means of triethylamine in THF providing the quinoxaline (VIII). Finally, this compound is hydrolyzed to the free phosphonic acid with trimethylbromo silane in acetonitrile.
| 【1】 Huth, A.; Turski, L. (Schering AG); Quinoxalindione derivs., their preparation and their use in drugs. DE 4314591; DE 4344486; EP 0696288; EP 1002796; JP 1996508037; US 5750525; WO 9425469 . |
| 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) | 28301 | 1,5-dichloro-2-nitro-4-(trifluoromethyl)benzene | 400-70-4 | C7H2Cl2F3NO2 | 详情 | 详情 |
| (II) | 28302 | aminomethylphosphonic acid | 1066-51-9 | CH6NO3P | 详情 | 详情 |
| (III) | 28303 | [5-chloro-2-nitro-4-(trifluoromethyl)anilino]methylphosphonic acid | C8H7ClF3N2O5P | 详情 | 详情 | |
| (IV) | 10388 | Morpholine | 110-91-8 | C4H9NO | 详情 | 详情 |
| (V) | 28304 | diethyl [5-(4-morpholinyl)-2-nitro-4-(trifluoromethyl)anilino]methylphosphonate | C16H23F3N3O6P | 详情 | 详情 | |
| (VI) | 28305 | diethyl [2-amino-5-(4-morpholinyl)-4-(trifluoromethyl)anilino]methylphosphonate | C16H25F3N3O4P | 详情 | 详情 | |
| (VII) | 11043 | Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride | 4755-77-5 | C4H5ClO3 | 详情 | 详情 |
| (VIII) | 28306 | diethyl [7-(4-morpholinyl)-2,3-dioxo-6-(trifluoromethyl)-3,4-dihydro-1(2H)-quinoxalinyl]methylphosphonate | C18H23F3N3O6P | 详情 | 详情 |